SU952102A3 - Способ получени 0-металлилоксифенола - Google Patents
Способ получени 0-металлилоксифенола Download PDFInfo
- Publication number
- SU952102A3 SU952102A3 SU792782748A SU2782748A SU952102A3 SU 952102 A3 SU952102 A3 SU 952102A3 SU 792782748 A SU792782748 A SU 792782748A SU 2782748 A SU2782748 A SU 2782748A SU 952102 A3 SU952102 A3 SU 952102A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- saturated
- water
- pyrocatechol
- alkyl
- aliphatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 229910001510 metal chloride Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000005826 halohydrocarbons Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 239000012429 reaction media Substances 0.000 abstract description 4
- 230000029936 alkylation Effects 0.000 abstract description 3
- 238000005804 alkylation reaction Methods 0.000 abstract description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 abstract 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- -1 2,3-dihydro-2,2-dimethyl-7-benzofuranyl Chemical group 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 229910001948 sodium oxide Inorganic materials 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229930195143 oxyphenol Natural products 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7819826A FR2434134A1 (fr) | 1978-06-26 | 1978-06-26 | Procede de preparation de l'o-methallyloxyphenol par monoetherification selective de la pyrocatechine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU952102A3 true SU952102A3 (ru) | 1982-08-15 |
Family
ID=9210267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792782748A SU952102A3 (ru) | 1978-06-26 | 1979-06-25 | Способ получени 0-металлилоксифенола |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4252985A (en:Method) |
| JP (1) | JPS557291A (en:Method) |
| AT (1) | AT371097B (en:Method) |
| BE (1) | BE877243A (en:Method) |
| BG (1) | BG35033A3 (en:Method) |
| BR (1) | BR7904035A (en:Method) |
| CA (1) | CA1131255A (en:Method) |
| CH (1) | CH639055A5 (en:Method) |
| DD (1) | DD144534A5 (en:Method) |
| DE (1) | DE2925763A1 (en:Method) |
| DK (1) | DK169099B1 (en:Method) |
| ES (1) | ES8107138A1 (en:Method) |
| FR (1) | FR2434134A1 (en:Method) |
| HU (1) | HU185608B (en:Method) |
| IE (1) | IE49177B1 (en:Method) |
| IL (1) | IL57539A (en:Method) |
| IT (1) | IT1121943B (en:Method) |
| LU (1) | LU81422A1 (en:Method) |
| NL (1) | NL188468C (en:Method) |
| PL (1) | PL119189B1 (en:Method) |
| PT (1) | PT69815A (en:Method) |
| RO (1) | RO77272A (en:Method) |
| SE (1) | SE448373B (en:Method) |
| SU (1) | SU952102A3 (en:Method) |
| YU (1) | YU41163B (en:Method) |
| ZA (1) | ZA793168B (en:Method) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2932458A1 (de) * | 1979-08-10 | 1981-02-26 | Bayer Ag | Herstellung von monoalkylethern von hydroxyphenolen und deren umwandlung zu hydroxycumaranen |
| US4390735A (en) * | 1980-10-22 | 1983-06-28 | Ciba-Geigy Corporation | Process for the preparation of p-allylphenols |
| DE3043230A1 (de) * | 1980-11-15 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | Herstellung von monoalkylaethern von hydroxyphenolen |
| US4465868A (en) * | 1981-07-17 | 1984-08-14 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing o-methallyloxyphenol |
| JPS6013036Y2 (ja) * | 1981-07-29 | 1985-04-25 | 石川島播磨重工業株式会社 | 熱処理炉 |
| IT1151718B (it) * | 1982-04-19 | 1986-12-24 | Brichima Spa | Procedimento per la preparazione del 2,3-diidro-2,2-dimetilbenzofuran-7-olo |
| IT1196002B (it) * | 1984-01-20 | 1988-11-10 | Brichima Spa | Procedimento per la sintesi di o-isopropossifenolo |
| US4639536A (en) * | 1984-08-30 | 1987-01-27 | Union Carbide Corporation | Intermediate, its synthesis, and its use in a process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| US4618728A (en) * | 1985-02-22 | 1986-10-21 | Fmc Corporation | Water aided catechol etherification |
| US4982012A (en) * | 1987-12-18 | 1991-01-01 | Fmc Corporation | Two phase process for preparing 2-methallyloxyphenol from catechol |
| WO1995034370A1 (en) * | 1994-06-13 | 1995-12-21 | Chiyoda Corporation | Gas-liquid contact gas dispersion pipe, and gas-liquid contact method and apparatus using the same |
| FR2772372B1 (fr) * | 1997-12-15 | 2000-05-19 | Rhodia Chimie Sa | Procede de o-alkylation de composes aromatiques hydroxyles |
| CN114307217A (zh) * | 2021-12-30 | 2022-04-12 | 江苏三吉利化工股份有限公司 | 一种呋喃酚废盐中提取邻甲代烯丙氧基苯酚的装置及方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474171A (en) * | 1964-01-23 | 1969-10-21 | Fmc Corp | 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate |
| US3274260A (en) * | 1964-08-31 | 1966-09-20 | Universal Oil Prod Co | Method for producing monoalkyl ethers of dihydric phenols |
| GB1227144A (en:Method) * | 1967-04-05 | 1971-04-07 | ||
| US3689570A (en) * | 1970-01-14 | 1972-09-05 | Peter S Gradeff | Monoalkylation of unsubstituted dihydric phenols with lower alkyl chlorides using alkali metal carbonates or bicarbonates as a condensing agent |
| US3927118A (en) * | 1973-12-21 | 1975-12-16 | Crown Zellerbach Corp | Process for monoetherification of polyhydric benzenes |
-
1978
- 1978-06-26 FR FR7819826A patent/FR2434134A1/fr active Granted
-
1979
- 1979-06-11 IL IL57539A patent/IL57539A/xx unknown
- 1979-06-12 ES ES481478A patent/ES8107138A1/es not_active Expired
- 1979-06-18 US US06/049,747 patent/US4252985A/en not_active Expired - Lifetime
- 1979-06-21 CH CH582079A patent/CH639055A5/fr not_active IP Right Cessation
- 1979-06-22 YU YU1482/79A patent/YU41163B/xx unknown
- 1979-06-22 CA CA330,364A patent/CA1131255A/en not_active Expired
- 1979-06-25 JP JP8063879A patent/JPS557291A/ja active Granted
- 1979-06-25 LU LU81422A patent/LU81422A1/fr unknown
- 1979-06-25 PL PL1979216591A patent/PL119189B1/pl unknown
- 1979-06-25 BG BG044043A patent/BG35033A3/xx unknown
- 1979-06-25 PT PT69815A patent/PT69815A/pt not_active IP Right Cessation
- 1979-06-25 BE BE0/195945A patent/BE877243A/xx not_active IP Right Cessation
- 1979-06-25 SE SE7905545A patent/SE448373B/sv not_active IP Right Cessation
- 1979-06-25 DK DK265779A patent/DK169099B1/da active
- 1979-06-25 SU SU792782748A patent/SU952102A3/ru active
- 1979-06-25 AT AT0443479A patent/AT371097B/de not_active IP Right Cessation
- 1979-06-26 HU HU79PI680A patent/HU185608B/hu not_active IP Right Cessation
- 1979-06-26 BR BR7904035A patent/BR7904035A/pt not_active IP Right Cessation
- 1979-06-26 DE DE19792925763 patent/DE2925763A1/de active Granted
- 1979-06-26 IT IT23875/79A patent/IT1121943B/it active
- 1979-06-26 RO RO7997963A patent/RO77272A/ro unknown
- 1979-06-26 NL NLAANVRAGE7904969,A patent/NL188468C/xx not_active IP Right Cessation
- 1979-06-26 DD DD79213901A patent/DD144534A5/de unknown
- 1979-08-08 IE IE1176/79A patent/IE49177B1/en not_active IP Right Cessation
- 1979-08-16 ZA ZA793168A patent/ZA793168B/xx unknown
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