CN116023238A - Preparation method of 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects - Google Patents
Preparation method of 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects Download PDFInfo
- Publication number
- CN116023238A CN116023238A CN202310322879.0A CN202310322879A CN116023238A CN 116023238 A CN116023238 A CN 116023238A CN 202310322879 A CN202310322879 A CN 202310322879A CN 116023238 A CN116023238 A CN 116023238A
- Authority
- CN
- China
- Prior art keywords
- chloro
- reaction
- mmol
- compound
- cleaning effects
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical class OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 230000000694 effects Effects 0.000 title claims abstract description 39
- 238000004140 cleaning Methods 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- 238000004659 sterilization and disinfection Methods 0.000 title claims abstract description 37
- 230000001954 sterilising effect Effects 0.000 title claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 122
- 238000000034 method Methods 0.000 claims abstract description 16
- 229940125904 compound 1 Drugs 0.000 claims abstract description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 9
- 229940125782 compound 2 Drugs 0.000 claims abstract description 8
- 238000000227 grinding Methods 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 229940126214 compound 3 Drugs 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- 230000005294 ferromagnetic effect Effects 0.000 claims description 30
- 238000001035 drying Methods 0.000 claims description 28
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 239000012074 organic phase Substances 0.000 claims description 24
- 239000000741 silica gel Substances 0.000 claims description 24
- 229910002027 silica gel Inorganic materials 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 238000004440 column chromatography Methods 0.000 claims description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 23
- 230000005291 magnetic effect Effects 0.000 description 22
- 238000012544 monitoring process Methods 0.000 description 12
- 244000005700 microbiome Species 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical class O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010303 mechanochemical reaction Methods 0.000 description 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Abstract
The invention discloses a preparation method of a 4-chloro-2-benzyl phenol derivative with sterilizing and cleaning effects, and belongs to the technical field of sterilization and disinfection. The preparation method comprises the following steps: in the presence of a phase transfer catalyst and alkali, reacting the compound 1 with the compound 2 under electromagnetic grinding to generate a target product compound 3;
Description
Technical Field
The invention relates to the technical field of sterilization and disinfection, in particular to a preparation method of a 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects.
Background
4-chloro-2-benzyl phenol (BCP) is an ingredient which is announced by the U.S. environmental protection agency to be allowed to be used for a surface cleaner for food contact, and is also an ingredient approved by the U.S. FDA for use in food processing machinery and container sterilization, and as a phenolic bactericide, 4-chloro-2-benzyl phenol (BCP) has been widely used in sterilization, disinfection, cleaning and the like in hospitals, hotels, public health facilities, households and the like, and has been widely used in recent years.
In 2007, documents Journal of the American Chemical Society, vol.54, p.3315, 3323 report that a method for preparing a 4-chloro-2-benzyl phenol derivative under mild preparation conditions and low cost needs to be developed by catalyzing alkylation reaction of phenol and alcohol under environment-friendly and heterogeneous reaction conditions with p-chlorophenol and benzyl alcohol as raw materials and UDCaT-5 (modified zirconia) as a catalyst to prepare a phenolic compound under high-temperature and high-pressure conditions in the reaction process.
Disclosure of Invention
The invention provides a preparation method of a 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects, which realizes the preparation of the 4-chloro-2-benzyl phenol derivative by using electromagnetic grinding equipment, has the advantages of simple operation method, mild reaction condition, quick reaction rate, higher yield, low-cost and easily obtained used basic medicines, low cost, simple process and less pollution, and is suitable for large-scale production.
The technical scheme of the invention is as follows:
a preparation method of a 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects comprises the following steps: in the presence of a phase transfer catalyst and alkali, reacting the compound 1 with the compound 2 under electromagnetic grinding to generate a target product compound 3;
r is-H, -CH 3 、-CN、-NO 2 One of-COOMe or-Cl.
Preferably, the ratio of compound 1 to compound 2 is 1 (1-2.5).
Preferably, the phase transfer catalyst is tetrabutylammonium bromide (Bu 4 NBr), benzyl triethylammonium chloride (C) 13 H 22 ClN), pyridine or tributylamine.
Preferably, the phase transfer catalyst is used in an amount of 5% to 25% of the compound 1 molar amount.
Preferably, the solvent is one of tetrahydrofuran, acetonitrile or N, N dimethylformamide.
Preferably, the base is potassium tert-butoxide (tBuOK) and the molar ratio of the amount of base to the amount of compound 1 is (1.5-2.5): 1.
Preferably, the electromagnetic grinding medium adopts a ferromagnetic rod, the ferromagnetic rod is made of SUS304 stainless steel, and the weight of the ferromagnetic rod is 7-10g.
Preferably, the reaction time is 1 to 3 hours.
Preferably, the specific preparation method is as follows: adding a phase transfer catalyst and alkali into a reaction bottle in an air environment, adding a compound 1 and a compound 2 into the reaction bottle, adding a solvent and a ferromagnetic rod, placing the reaction bottle into a reactor for reaction for 1-3h, cooling the system to room temperature after the reaction is finished, dissolving out a mixture in the bottle by using an organic solvent, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, performing column chromatography, and separating to obtain a target product.
Compared with the prior art, the invention has the following beneficial effects:
1. the preparation method is a mechanochemical method, the power of the mechanochemical reaction is mechanical energy rather than thermal energy, so that the reaction can be completed without harsh conditions such as high temperature, high pressure and the like, the reaction cost is low, the yield is high, the process is simple, the pollution is less, the special ferromagnetic rod can be recycled, the raw materials used in the preparation method are mature and efficient in preparation route, the performance is very stable, and special preservation conditions are not needed; 2. the preparation of the 4-chloro-2-benzyl phenol derivative is realized by using electromagnetic grinding equipment, the operation method is simple, the reaction condition is mild, the reaction rate is high, the used basic medicines are cheap and easy to obtain, and the preparation method has the characteristics of low cost, high yield, simple process and less pollution, and is suitable for large-scale production.
Detailed Description
The process, conditions, reagents, experimental methods, etc., for carrying out the present invention will be described in further detail with reference to the following specific examples, which are conventional in the art, except as specifically mentioned below.
In the following examples, compound 1a corresponds to compound 1, compounds 2a to 2e correspond to compound 2, and compounds 3a to 3e correspond to compound 3.
Example 1
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 1 hour. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 36%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 2
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 2 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving the mixture in the bottle by using ethyl acetate, extracting with water for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin-drying, performing column chromatography, and separating to obtain a target product 3a with the yield of 53%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 3
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 86%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 4
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,1.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 36%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 5
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,1.5 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving the mixture in the bottle by using ethyl acetate, extracting with water for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin-drying, performing column chromatography, and separating to obtain a target product 3a with the yield of 53%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 6
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.5 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 81%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 7
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.05 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 26%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 8
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.25 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 82%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 9
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 7g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 75%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 10
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 10g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 81%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 11
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (1.5 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 72%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 12
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.5 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. And monitoring the reaction progress by TLC, namely determining the reaction completion, cooling the system to room temperature after the reaction completion, dissolving out the mixture in the bottle by using ethyl acetate, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, carrying out column chromatography, and separating to obtain a target product 3a with the yield of 86%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 13
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
benzyl triethyl ammonium chloride (C) was added to the reaction flask under an air atmosphere 13 H 22 ClN) (0.2 mmol), potassium t-butoxide (2.0 mmol), then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask, followed by 4mL of tetrahydrofuran, and finally 8g of ferromagnetic rods. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with methylene chloride, extracted three times with water, the upper organic phase was taken, dried with anhydrous sodium sulfate, dried with silica gel, column-chromatographed, and the target product 3a was isolated in 70% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 14
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
pyridine (0.2 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. The progress of the reaction was monitored by TLC, after completion of the reaction, the system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product 3a was isolated in 25% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 15
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tributylamine (0.2 mmol), potassium t-butoxide (2 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. The reaction progress was monitored by TLC, after the reaction was completed, the system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried with anhydrous sodium sulfate, dried with silica gel, and subjected to column chromatography, and the yield of the target product 3a was separated to 20%.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 16
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of acetonitrile was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product 3a was isolated in 30% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 17
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and 4-chlorophenol (1 a,1.0 mmol) and toluene (2 a,2.0 mmol) were added to the reaction flask under air, 4mL of N, N dimethylformamide were added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product 3a was isolated in 32% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.83(s, 1H), 7.29-7.25(m, 2H), 7.21(m, 1H), 7.09(d,J= 8.0 Hz, 1H), 6.68(d,J= 8.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 3.91(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 150.9, 138.9, 129.1, 129.0, 128.9, 128.8, 126.9, 125.4, 36.6.
HRMS (ESI) calculated as C 20 H 17 Ocl+h, 219.0580, actual value 219.0577.
Example 18
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and metaxylene (2 b,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added thereto, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product 3b was isolated in 53% yield.
1 H NMR (400 MHz, CDCl 3 , δppm):8.82(s, 1H) 7.17-7.05(m, 6H), 6.81(d,J= 4.0 Hz, 1H), 3.99(s, 2H), 2.232(s, 3H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 152.72, 137.23, 129.89, 129.90, 128.46, 117.00, 35.61, 21.13
HRMS (ESI) calculated as C 14 H 13 Ocl+h, 223.0737, actual value 223.0733.
Example 19
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium tert-butoxide, was added to the reaction flask under air
(2.0 mmol) then 4-chlorophenol (1 a,1.0 mmol) and o-methylbenzonitrile (2 c,2.0 mmol) were added to the reaction flask, 4mL tetrahydrofuran was added, and finally 8g ferromagnetic bars were added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the yield of the target product 3c was 78% by separation.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.72(s, 1H) 7.61-7.60(s, 1H), 7.45-7.40(m, 2H), 7.28(d,J= 4.0 Hz, 1H), 7.18(dd,J= 4.0 Hz, 1H), 7.00(d,J=8.0 Hz, 2H), 6.82(d,J= 8Hz, 1H), 3.92(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 153.83, 139.20, 126.19, 130.62, 130.29, 129.34, 128.89, 118.52, 116.95, 112.05, 35.25.
HRMS (ESI) calculated as C 14 H 10 Clno+h, 244.0534, actual value 244.0529.
Example 20
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and o-methylnitrobenzene (2 d,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product was isolated in 73% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.75(s, 1H) 8.14(d,J=4 Hz, 1H) ,8.04(s, 1H), 7.49(t,J= 6.0Hz, 1H), 7.36(d,J=4.0Hz, 1H), 7.18(d,J=8.0 Hz, 1H), 7.10(s, 1H), 6.83(d,J=8Hz, 1H), 3.96(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 153.92, 148.47, 39.11, 13382, 129.48, 127.79, 123.10, 122.69, 116.97, 34.79.
HRMS (ESI) calculated as C 13 H 10 ClNO 3 +H, 264.0432, actual value 264.0427.
Example 21
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and methyl p-methylbenzoate (2 e,2.0 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product 3e was isolated in 82% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):9.04(s, 1H) 7.95(d,J= 8.0 Hz, 2H), 7.19(d,J= 8.0 Hz, 1H), 7.10-7.08(m, 3H), 6.82(d,J=4.0 Hz, 1H), 3.92(s, 2H), 3.88(s, 3H)
13 C NMR (100 MHz, CDCl 3 ,δppm): 165.91, 153.01, 141.29, 130.34, 129.10, 128.67, 127.79, 116.96, 52.19, 35.71.
HRMS (ESI) calculated as C 15 H 13 ClO 3 +H, 277.0635, actual value 277.0631.
Example 22
The preparation method of the 4-chloro-2-benzyl phenol derivative with the sterilization and cleaning effects in the embodiment comprises the following steps:
tetrabutylammonium bromide (0.2 mmol), potassium t-butoxide (2.0 mmol) and then 4-chlorophenol (1 a,1.0 mmol) and m-chlorotoluene (2 e,2 mmol) were added to the reaction flask under air, 4mL of tetrahydrofuran was added, and finally 8g of ferromagnetic rod was added. The reaction flask was placed in a magnetic mill and reacted for 3 hours. After the reaction progress was monitored by TLC, the reaction was completed, the system was cooled to room temperature, the mixture in the flask was dissolved with ethyl acetate, extracted three times with water, the upper organic phase was taken, dried over anhydrous sodium sulfate, dried over silica gel, column chromatography, and the target product 3e was isolated in 52% yield.
1 H NMR (400 MHz, CDCl 3 , δ ppm):8.87(s, 1H), 7.31-7.09 (m, 6H), 6.82 (d,J= 4.0 Hz, 1H), 3.92(s, 2H).
13 C NMR (100 MHz, CDCl 3 , δ ppm): 153.90, 139.14, 134.35, 129.95, 129.30, 129.07, 128.47, 128.8, 127.97, 127.61, 117.02, 35.36.
HRMS (ESI) calculated as C 13 H 10 Cl 2 O+h, 253.0187, actual value 253.0184.
The sterilization conditions of the 4-chloro-2-benzyl phenol derivatives prepared in examples 17 to 18 and examples 20 to 22 are explored, the quantitative sterilization test of the suspension in the sterilization technical specification (2002 edition) is referred, 3 times of repeated tests are carried out, and under the constant temperature test condition of 20 ℃, the 4-chloro-2-benzyl phenol derivative sample diluted 128 times is applied to act on escherichia coli, staphylococcus aureus, pseudomonas aeruginosa and candida albicans for 5.0min respectively. The sterilization conditions of the 4-chloro-2-benzylphenol derivatives prepared in examples 17 to 18 and examples 20 to 22 are shown in tables 1 to 5, respectively.
TABLE 1
TABLE 2
TABLE 3 Table 3
TABLE 4 Table 4
TABLE 5
As can be seen from tables 1-5, the 4-chloro-2-benzyl phenol derivative prepared by the method has the effects on escherichia coli, staphylococcus aureus, pseudomonas aeruginosa and candida albicans for 5.0min, the killing pair number is more than 6.00, namely the killing efficiency on the microorganisms is more than 99.9999%, and the killing pair number is more than 4.00 when the quantitative killing test of the laboratory microorganisms is carried out by adopting a suspension method according to the microorganism killing index of national standard GB/T27947-2020 "phenolic disinfectant health requirement". According to the results, the 4-chloro-2-benzyl phenol derivative prepared by the method has good bactericidal performance and has the effect of killing microorganisms reaching the national standard.
Claims (9)
1. The preparation method of the 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects is characterized by comprising the following steps of: in the presence of a phase transfer catalyst and alkali, reacting the compound 1 with the compound 2 under electromagnetic grinding to generate a target product compound 3;
r is-H, -CH 3 、-CN、-NO 2 One of-COOMe or-Cl.
2. The method for producing a 4-chloro-2-benzylphenol derivative having antibacterial and cleaning effects according to claim 1, wherein the molar ratio of compound 1 to compound 2 is 1 (1-2.5).
3. The method for preparing a 4-chloro-2-benzylphenol derivative having bactericidal and cleaning effects according to claim 1, wherein the phase transfer catalyst is one of tetrabutylammonium bromide, benzyltriethylammonium chloride, pyridine or tributylamine.
4. The method for producing a 4-chloro-2-benzylphenol derivative having antibacterial and cleaning effects according to claim 1, wherein the amount of the phase transfer catalyst is 5 to 25% of the amount of 1 mol of the compound.
5. The method for preparing a 4-chloro-2-benzylphenol derivative having bactericidal and cleaning effects according to claim 1, wherein the solvent is one of tetrahydrofuran, acetonitrile or N, N-dimethylformamide.
6. The method for producing a 4-chloro-2-benzylphenol derivative having antibacterial and cleaning effects according to claim 1, wherein the base is potassium t-butoxide and the molar ratio of the amount of the base to the amount of the compound 1 is (1.5-2.5): 1.
7. The method for preparing a 4-chloro-2-benzylphenol derivative with sterilizing and cleaning effects according to claim 1, wherein the electromagnetic grinding medium is a ferromagnetic rod made of SUS304 stainless steel, and the weight of the ferromagnetic rod is 7-10g.
8. The method for producing a 4-chloro-2-benzylphenol derivative having antibacterial and cleaning effects according to claim 1, wherein the reaction time is 1 to 3 hours.
9. The method for producing a 4-chloro-2-benzylphenol derivative having antibacterial and cleaning effects according to claim 7, which is characterized by comprising the following steps: adding a phase transfer catalyst and alkali into a reaction bottle in an air environment, adding a compound 1 and a compound 2 into the reaction bottle, adding a solvent and a ferromagnetic rod, placing the reaction bottle into a reactor for reaction for 1-3h, cooling the system to room temperature after the reaction is finished, dissolving out a mixture in the bottle by using an organic solvent, adding water for extraction for three times, taking an upper organic phase, adding anhydrous sodium sulfate for drying, adding silica gel for spin drying, performing column chromatography, and separating to obtain a target product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310322879.0A CN116023238A (en) | 2023-03-30 | 2023-03-30 | Preparation method of 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310322879.0A CN116023238A (en) | 2023-03-30 | 2023-03-30 | Preparation method of 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116023238A true CN116023238A (en) | 2023-04-28 |
Family
ID=86089684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310322879.0A Pending CN116023238A (en) | 2023-03-30 | 2023-03-30 | Preparation method of 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116023238A (en) |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR884416A (en) * | 1939-12-05 | 1943-08-12 | Deutsche Hydrierwerke Ag | Process for the preparation of aralkylated phenols and products obtained by this process |
| GB1096441A (en) * | 1964-01-15 | 1967-12-29 | Bristol Myers Co | Ethers of benzyl phenols and a process for the preparation thereof |
| US4187084A (en) * | 1978-07-03 | 1980-02-05 | Khomich Nikolai S | Ferromagnetic abrasive material and method for preparing the same |
| US5414156A (en) * | 1993-09-08 | 1995-05-09 | Dong Kook Pharmaceutical Co., Ltd. | Process for producing ortho-isopropylated phenol derivatives |
| US20110117034A1 (en) * | 2007-11-12 | 2011-05-19 | Kenya Satonaka | Ultraviolet absorber water-dispersed composition |
| US20160060278A1 (en) * | 2014-09-02 | 2016-03-03 | California Institute Of Technology | Base-catalyzed silylation of terminal alkyne c-h bonds |
| US20180057443A1 (en) * | 2016-08-26 | 2018-03-01 | Massachusetts Institute Of Technology | Mechanochemical synthesis of iptycenes |
| US20200048243A1 (en) * | 2015-12-16 | 2020-02-13 | Brandeis University | Cinchonine-derived catalysts and methods of using same |
| WO2022155936A1 (en) * | 2021-01-22 | 2022-07-28 | 苏州大学 | Method for synthesizing aryl benzyl ether compound |
| CN115572240A (en) * | 2022-10-19 | 2023-01-06 | 西安交通大学 | Mechanical force synthesis method for constructing C-C bond by three-component reduction cross coupling |
-
2023
- 2023-03-30 CN CN202310322879.0A patent/CN116023238A/en active Pending
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR884416A (en) * | 1939-12-05 | 1943-08-12 | Deutsche Hydrierwerke Ag | Process for the preparation of aralkylated phenols and products obtained by this process |
| GB1096441A (en) * | 1964-01-15 | 1967-12-29 | Bristol Myers Co | Ethers of benzyl phenols and a process for the preparation thereof |
| US4187084A (en) * | 1978-07-03 | 1980-02-05 | Khomich Nikolai S | Ferromagnetic abrasive material and method for preparing the same |
| US5414156A (en) * | 1993-09-08 | 1995-05-09 | Dong Kook Pharmaceutical Co., Ltd. | Process for producing ortho-isopropylated phenol derivatives |
| US20110117034A1 (en) * | 2007-11-12 | 2011-05-19 | Kenya Satonaka | Ultraviolet absorber water-dispersed composition |
| US20160060278A1 (en) * | 2014-09-02 | 2016-03-03 | California Institute Of Technology | Base-catalyzed silylation of terminal alkyne c-h bonds |
| US20200048243A1 (en) * | 2015-12-16 | 2020-02-13 | Brandeis University | Cinchonine-derived catalysts and methods of using same |
| US20180057443A1 (en) * | 2016-08-26 | 2018-03-01 | Massachusetts Institute Of Technology | Mechanochemical synthesis of iptycenes |
| WO2022155936A1 (en) * | 2021-01-22 | 2022-07-28 | 苏州大学 | Method for synthesizing aryl benzyl ether compound |
| CN115572240A (en) * | 2022-10-19 | 2023-01-06 | 西安交通大学 | Mechanical force synthesis method for constructing C-C bond by three-component reduction cross coupling |
Non-Patent Citations (2)
| Title |
|---|
| LEI-LEI BIE 等: "Selective hydrogenolysis of Csingle bondO bonds in benzyloxybenzene and dealkaline lignin to valuable aromatics over Ni/TiN", FUEL PROCESSING TECHNOLOGY, vol. 209, pages 106523 - 106532 * |
| 曾令可等: "纳米陶瓷技术", 华南理工大学出版社, pages: 137 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107711855B (en) | Application of camelinine A derivative in preparation of medicines for preventing and treating or resisting plant diseases | |
| CN116023238A (en) | Preparation method of 4-chloro-2-benzyl phenol derivative with sterilization and cleaning effects | |
| CN106699722B (en) | A kind of fluoro- 1,3- benzo two of 2,2- bis- dislikes the synthetic method of cyclopentadienyl -4- formaldehyde | |
| CN113234070A (en) | Honokiol thioether derivative containing oxazole ring, and preparation method and application thereof | |
| CN109651367B (en) | Method for preparing 1, 4-dihydroquinoline and pyrrolo [1,2-a ] quinoline compounds | |
| Zheng et al. | Synthesis of allyl-type selenides and α-selenoesters in Aqueous Media Promoted by Cadmium | |
| CN108485987B (en) | Dibenzoxepin compound and preparation method and application thereof | |
| CN114394884B (en) | Preparation method of allylphenol compound | |
| Grivas et al. | Palladium (0)‐catalyzed phenylation of imidazo [4, 5‐b] pyridines | |
| CN103030608B (en) | N-(5-dehydroabietyl-[1, 3, 4] thiadiazole-2-yl)-amide derivative and preparation method and application thereof | |
| JPS5814428B2 (en) | Isomerization method for stereoisomeric alicyclic diamines | |
| CN100432037C (en) | Bromo-2, 4'-dihydroxy diphenyl ether compound and its synthesizing method | |
| CN109503612B (en) | Structure modifier of 8-methoxypsoralen and preparation method and application thereof | |
| US4183861A (en) | Process for preparing aromatic methylene-dioxy compounds | |
| CN108752218A (en) | A kind of variation route prepared by Du Lutewei key intermediates 2,4- difluorobenzylamines | |
| CN114478467B (en) | Fluoro-cyclohexanone spiro 1, 3-dioxane chiral derivative and preparation method thereof | |
| JPH05286882A (en) | Production of 2,3-difluorophenols | |
| CN106631968A (en) | Method for preparing indole and derivatives thereof | |
| CN115784978B (en) | Method for synthesizing 2-amino-6-bromopyridine | |
| JPH03279348A (en) | Production of 2,4,5-trifluoro-3-alkoxybenzoic acid | |
| Gilchrist et al. | A new route to 3-alkoxypyridine 1-oxides | |
| CN108822060B (en) | 3-aryl substituted oxetane and preparation method thereof | |
| CN107188878B (en) | Antibacterial agent and synthesis method and application thereof | |
| CN117164595A (en) | Coumarin derivative, preparation method thereof and application of coumarin derivative as plant pathogenic fungi bacteriostat | |
| CN115232101A (en) | 1-acyloxy sesame phenol derivative and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20230428 |