SK119493A3 - Method of preparation 2-alkyl-4-acyl-6-tere-butylphenol compounds - Google Patents
Method of preparation 2-alkyl-4-acyl-6-tere-butylphenol compounds Download PDFInfo
- Publication number
- SK119493A3 SK119493A3 SK1194-93A SK119493A SK119493A3 SK 119493 A3 SK119493 A3 SK 119493A3 SK 119493 A SK119493 A SK 119493A SK 119493 A3 SK119493 A3 SK 119493A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- tert
- butylphenol
- carbon atoms
- acyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000011541 reaction mixture Substances 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 239000000376 reactant Substances 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 19
- 239000013078 crystal Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000012452 mother liquor Substances 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 abstract 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical group CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- -1 Acyl Trifluoroacetates Chemical class 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZHXUEUKVDMWSKV-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)hex-5-yn-1-one Chemical compound CC(C)(C)C1=CC(C(=O)CCCC#C)=CC(C(C)(C)C)=C1O ZHXUEUKVDMWSKV-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- YUEIEICXHOXYPZ-UHFFFAOYSA-N CC(C)(C)C1=CC(C(=O)CCC=C=C)=CC(C(C)(C)C)=C1O Chemical compound CC(C)(C)C1=CC(C(=O)CCC=C=C)=CC(C(C)(C)C)=C1O YUEIEICXHOXYPZ-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- VPFMEXRVUOPYRG-UHFFFAOYSA-N hex-5-ynoic acid Chemical compound OC(=O)CCCC#C VPFMEXRVUOPYRG-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/675,384 US5126487A (en) | 1991-03-26 | 1991-03-26 | Process for the preparation of 2-alkyl-4-acyl-6-tert-butylphenol compounds |
| PCT/US1992/000817 WO1992017432A1 (en) | 1991-03-26 | 1992-01-31 | Process for the preparation of 2-alkyl-4-acyl-6-tert-butylphenol compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK119493A3 true SK119493A3 (en) | 1994-09-07 |
Family
ID=24710249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1194-93A SK119493A3 (en) | 1991-03-26 | 1992-01-31 | Method of preparation 2-alkyl-4-acyl-6-tere-butylphenol compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5126487A (cs) |
| EP (1) | EP0593497B1 (cs) |
| JP (1) | JPH06506223A (cs) |
| KR (1) | KR100201518B1 (cs) |
| AT (1) | ATE153994T1 (cs) |
| AU (1) | AU666845B2 (cs) |
| CA (1) | CA2106786C (cs) |
| CZ (1) | CZ281464B6 (cs) |
| DE (1) | DE69220226T2 (cs) |
| DK (1) | DK0593497T3 (cs) |
| ES (1) | ES2103945T3 (cs) |
| GR (1) | GR3024006T3 (cs) |
| HU (1) | HU213038B (cs) |
| NZ (1) | NZ242118A (cs) |
| PL (1) | PL169009B1 (cs) |
| SK (1) | SK119493A3 (cs) |
| WO (1) | WO1992017432A1 (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633594B (zh) * | 2009-08-20 | 2012-12-05 | 镇江市海通化工有限公司 | 一种环保的傅克反应后处理方法 |
| CN103804158B (zh) * | 2012-11-02 | 2018-06-01 | Dic株式会社 | 受阻酚的制造方法及其制造中间体 |
| JP6302157B2 (ja) * | 2012-11-02 | 2018-03-28 | Dic株式会社 | ヒンダードフェノールの製造方法 |
| EP3813948A1 (en) | 2018-06-27 | 2021-05-05 | Cornell University | Substituted alkylphenols as hcn1 antagonists |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4708966A (en) * | 1986-06-27 | 1987-11-24 | The Procter & Gamble Company | Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation |
| US4849428A (en) * | 1987-11-23 | 1989-07-18 | The Procter & Gamble Company | Cyclic anti-inflammatory derivatives of di-tert-butylphenol compounds, compositions and use |
| US4847303A (en) * | 1987-11-23 | 1989-07-11 | The Procter & Gamble Company | Tert-butylphenyl compounds useful as anti-inflammatory agents |
| IL88674A0 (en) * | 1987-12-18 | 1989-07-31 | Norwich Eaton Pharma | Preparation of certain substituted aromatic compounds |
| US4982006A (en) * | 1987-12-18 | 1991-01-01 | Norwich Eaton Pharmaceuticals, Inc. | Process for the preparation of certain substituted aromatic compounds |
-
1991
- 1991-03-26 US US07/675,384 patent/US5126487A/en not_active Expired - Fee Related
-
1992
- 1992-01-31 DK DK92909974.5T patent/DK0593497T3/da active
- 1992-01-31 HU HU9302972A patent/HU213038B/hu not_active IP Right Cessation
- 1992-01-31 EP EP92909974A patent/EP0593497B1/en not_active Expired - Lifetime
- 1992-01-31 WO PCT/US1992/000817 patent/WO1992017432A1/en active IP Right Grant
- 1992-01-31 CA CA002106786A patent/CA2106786C/en not_active Expired - Fee Related
- 1992-01-31 PL PL92300713A patent/PL169009B1/pl unknown
- 1992-01-31 AT AT92909974T patent/ATE153994T1/de active
- 1992-01-31 KR KR1019930702887A patent/KR100201518B1/ko not_active Expired - Fee Related
- 1992-01-31 CZ CS932259A patent/CZ281464B6/cs not_active IP Right Cessation
- 1992-01-31 SK SK1194-93A patent/SK119493A3/sk unknown
- 1992-01-31 AU AU17470/92A patent/AU666845B2/en not_active Ceased
- 1992-01-31 DE DE69220226T patent/DE69220226T2/de not_active Expired - Fee Related
- 1992-01-31 ES ES92909974T patent/ES2103945T3/es not_active Expired - Lifetime
- 1992-01-31 JP JP4509319A patent/JPH06506223A/ja active Pending
- 1992-03-25 NZ NZ242118A patent/NZ242118A/en unknown
-
1997
- 1997-07-08 GR GR970401659T patent/GR3024006T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2106786A1 (en) | 1992-09-27 |
| EP0593497B1 (en) | 1997-06-04 |
| PL169009B1 (pl) | 1996-05-31 |
| HUT66567A (en) | 1994-12-28 |
| GR3024006T3 (en) | 1997-10-31 |
| CA2106786C (en) | 1997-12-09 |
| KR100201518B1 (ko) | 1999-06-15 |
| DE69220226T2 (de) | 1998-01-08 |
| ES2103945T3 (es) | 1997-10-01 |
| WO1992017432A1 (en) | 1992-10-15 |
| CZ281464B6 (cs) | 1996-10-16 |
| JPH06506223A (ja) | 1994-07-14 |
| HU213038B (en) | 1997-01-28 |
| HU9302972D0 (en) | 1994-01-28 |
| EP0593497A1 (en) | 1994-04-27 |
| NZ242118A (en) | 1995-03-28 |
| AU1747092A (en) | 1992-11-02 |
| CZ225993A3 (en) | 1994-04-13 |
| DE69220226D1 (de) | 1997-07-10 |
| US5126487A (en) | 1992-06-30 |
| AU666845B2 (en) | 1996-02-29 |
| DK0593497T3 (da) | 1997-10-27 |
| ATE153994T1 (de) | 1997-06-15 |
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