JP4764416B2 - ヒドロキシスチレンおよびそのアセチル化誘導体を製造する方法 - Google Patents
ヒドロキシスチレンおよびそのアセチル化誘導体を製造する方法 Download PDFInfo
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- JP4764416B2 JP4764416B2 JP2007505052A JP2007505052A JP4764416B2 JP 4764416 B2 JP4764416 B2 JP 4764416B2 JP 2007505052 A JP2007505052 A JP 2007505052A JP 2007505052 A JP2007505052 A JP 2007505052A JP 4764416 B2 JP4764416 B2 JP 4764416B2
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- Prior art keywords
- phca
- hydroxystyrene
- decarboxylation
- reaction
- reaction mixture
- 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.)
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- 239000012454 non-polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
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- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- UEEZMPKIFPDZLX-ONEGZZNKSA-N (e)-3-(4-hydroxy-3,5-dimethylphenyl)prop-2-enoic acid Chemical compound CC1=CC(\C=C\C(O)=O)=CC(C)=C1O UEEZMPKIFPDZLX-ONEGZZNKSA-N 0.000 description 1
- 0 *C([C@@]1C(*)=C(*)C(*)=C(*)C1I)=C(*)C(O)=O Chemical compound *C([C@@]1C(*)=C(*)C(*)=C(*)C1I)=C(*)C(O)=O 0.000 description 1
- ZMRCFZFFKWFWSK-UHFFFAOYSA-N 2,6-ditert-butyl-4-ethenylphenol Chemical compound CC(C)(C)C1=CC(C=C)=CC(C(C)(C)C)=C1O ZMRCFZFFKWFWSK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 102100034082 Alkaline ceramidase 3 Human genes 0.000 description 1
- 108010004032 Bromelains Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000223233 Cutaneotrichosporon cutaneum Species 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 101000798828 Homo sapiens Alkaline ceramidase 3 Proteins 0.000 description 1
- QXAGXXMAXUVQSF-UHFFFAOYSA-N OC1=CC=CC=C1C=C.OC1=CC=C(C=C)C=C1O Chemical compound OC1=CC=CC=C1C=C.OC1=CC=C(C=C)C=C1O QXAGXXMAXUVQSF-UHFFFAOYSA-N 0.000 description 1
- 108700023158 Phenylalanine ammonia-lyases Proteins 0.000 description 1
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- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 102000005158 Subtilisins Human genes 0.000 description 1
- 108010056079 Subtilisins Proteins 0.000 description 1
- JZSNFWFYDNQTHM-UHFFFAOYSA-N [4-(1-cyanoethenyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C(=C)C#N)C=C1 JZSNFWFYDNQTHM-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000007514 bases Chemical group 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000019835 bromelain Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- XDZLHTBOHLGGCJ-UHFFFAOYSA-N hexyl 2-cyanoprop-2-enoate Chemical compound CCCCCCOC(=O)C(=C)C#N XDZLHTBOHLGGCJ-UHFFFAOYSA-N 0.000 description 1
- 229930005346 hydroxycinnamic acid Natural products 0.000 description 1
- 235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000009629 microbiological culture 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
- 238000010369 molecular cloning Methods 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 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
- 239000000725 suspension Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- 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
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55686104P | 2004-03-26 | 2004-03-26 | |
| US60/556,861 | 2004-03-26 | ||
| PCT/US2005/009290 WO2005097719A1 (en) | 2004-03-26 | 2005-03-21 | A method for preparing hydroxystyrenes and acetylated derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007530548A JP2007530548A (ja) | 2007-11-01 |
| JP2007530548A5 JP2007530548A5 (enExample) | 2008-05-08 |
| JP4764416B2 true JP4764416B2 (ja) | 2011-09-07 |
Family
ID=35124980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007505052A Expired - Fee Related JP4764416B2 (ja) | 2004-03-26 | 2005-03-21 | ヒドロキシスチレンおよびそのアセチル化誘導体を製造する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7586013B2 (enExample) |
| JP (1) | JP4764416B2 (enExample) |
| CN (1) | CN1934061A (enExample) |
| DE (1) | DE112005000464T5 (enExample) |
| TW (1) | TW200600493A (enExample) |
| WO (1) | WO2005097719A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007086559A1 (ja) * | 2006-01-27 | 2007-08-02 | Ube Industries, Ltd. | テトラヒドロピラン化合物の製造方法 |
| JP5600003B2 (ja) * | 2006-08-01 | 2014-10-01 | デュポン エレクトロニック ポリマーズ リミテッド パートナーシップ | フェノール材料からポリマーを調製する方法およびこれに関連する組成物 |
| US7468415B2 (en) * | 2007-01-04 | 2008-12-23 | E. I. Du Pont De Nemours And Company | Method for preparing glycidyloxystyrene monomers and polymers thereof |
| JP5526948B2 (ja) * | 2010-03-31 | 2014-06-18 | ユーハ味覚糖株式会社 | ２，６−ジプレニル−４−ビニルフェノールの生成方法 |
| CN102001918B (zh) * | 2010-09-27 | 2013-12-18 | 常州大学 | 对羟基苯乙烯及其衍生物的制备方法 |
| CN103086884A (zh) * | 2012-12-14 | 2013-05-08 | 湖南科源生物制品有限公司 | 乙酰化白藜芦醇的半合成方法 |
| JP6008201B2 (ja) * | 2013-05-10 | 2016-10-19 | 東レ・ファインケミカル株式会社 | スチレン誘導体の製造方法 |
| JP6094969B2 (ja) * | 2013-06-24 | 2017-03-15 | 東レ・ファインケミカル株式会社 | ヒドロキシスチレン誘導体の製造方法 |
| CN108129318A (zh) * | 2018-01-30 | 2018-06-08 | 上海博栋化学科技有限公司 | 一种3，4-二乙酰氧基苯乙烯的制备方法 |
| CN108658731B (zh) * | 2018-06-01 | 2022-05-06 | 巨野现代精细化工有限公司 | 一种对羟基苯乙烯的合成方法 |
| KR20220044564A (ko) | 2019-08-09 | 2022-04-08 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 화합물, 중합체, 조성물, 막형성용 조성물, 패턴형성방법, 절연막의 형성방법 및 화합물의 제조방법, 그리고 요오드함유 비닐폴리머 및 그의 아세틸화유도체의 제조방법 |
| TWI836227B (zh) * | 2020-06-18 | 2024-03-21 | 日商丸善石油化學股份有限公司 | 高純度４－羥基苯乙烯溶液、其製造方法及４－羥基苯乙烯系聚合物的製造方法 |
| CN114773191A (zh) * | 2022-04-29 | 2022-07-22 | 四川东材科技集团成都新材料有限公司 | 一种一锅法制备对乙酰氧基苯乙烯的方法 |
| TW202440507A (zh) | 2022-12-20 | 2024-10-16 | 日商三菱瓦斯化學股份有限公司 | 化合物之製造方法、聚合物、組成物、圖型形成方法 |
| CN115974659B (zh) * | 2022-12-29 | 2024-08-09 | 徐州博康信息化学品有限公司 | 一种1-(1-乙氧基乙氧基)-4-乙烯基苯的合成方法 |
| CN116924907A (zh) * | 2023-06-05 | 2023-10-24 | 成都东凯芯半导体材料有限公司 | 一种一锅法制备3,4-二乙酰氧基苯乙烯的方法 |
| TW202528272A (zh) * | 2023-09-08 | 2025-07-16 | 日商丸善石油化學股份有限公司 | 高純度ｏ－／ｍ－羥基苯乙烯溶液、其製造方法及ｏ－／ｍ－羥基苯乙烯系聚合物之製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316995A (en) * | 1981-02-05 | 1982-02-23 | International Flavors & Fragrances Inc. | Process for preparing vinyl phenol |
| JP2004231524A (ja) * | 2003-01-28 | 2004-08-19 | Wakayama Prefecture | スチレン誘導体の製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3100447C2 (de) * | 1981-01-09 | 1983-02-24 | Volker Dipl.-Chem. 6000 Frankfurt Genrich | Fensterzählrohr und Verfahren zu seiner Herstellung |
| US5084533A (en) * | 1988-07-19 | 1992-01-28 | Hoechst Celanese Corporation | Neat (solventless) hydrogenation of 4-acetoxyacetophenone in the production of 4-acetoxystyrene and its polymers and hydrolysis products |
| US5245074A (en) * | 1988-07-19 | 1993-09-14 | Shah Bakulesh N | Process for the production of 4-acetoxystyrene, its polymers and hydrolysis products |
| US5151546A (en) * | 1988-07-19 | 1992-09-29 | Hoechst Celanese Corporation | Process for the production of 4-acetoxystyrene, its polymers and hydrolysis products |
| US5041614A (en) * | 1990-07-03 | 1991-08-20 | Hoechst Celanese Corporation | Method for the preparation of 4-acetoxystyrene |
| US5136083A (en) * | 1990-08-30 | 1992-08-04 | Hoechst Celanese Corporation | Process for the purification of 4-acetoxystyrene |
| EP0502819A1 (de) * | 1991-03-01 | 1992-09-09 | Ciba-Geigy Ag | Säurekatalytisch vernetzbare Copolymere |
| TW304235B (enExample) * | 1992-04-29 | 1997-05-01 | Ocg Microelectronic Materials | |
| US5453481A (en) * | 1995-03-01 | 1995-09-26 | Hoechst Celanese Corporation | Process for preparing vinylphenol polymers and copolymers |
| US5563289A (en) * | 1995-10-13 | 1996-10-08 | Hoechst Celanese Corporation | Process for preparing acetoxystyrene |
| US5578687A (en) * | 1995-10-13 | 1996-11-26 | Hoechst Celanese Corporation | Process for preparing poly(4-hydroxystyrene) |
-
2005
- 2005-03-17 US US11/082,258 patent/US7586013B2/en not_active Expired - Fee Related
- 2005-03-21 WO PCT/US2005/009290 patent/WO2005097719A1/en not_active Ceased
- 2005-03-21 DE DE112005000464T patent/DE112005000464T5/de not_active Withdrawn
- 2005-03-21 CN CNA2005800095674A patent/CN1934061A/zh active Pending
- 2005-03-21 JP JP2007505052A patent/JP4764416B2/ja not_active Expired - Fee Related
- 2005-03-25 TW TW094109225A patent/TW200600493A/zh unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316995A (en) * | 1981-02-05 | 1982-02-23 | International Flavors & Fragrances Inc. | Process for preparing vinyl phenol |
| JP2004231524A (ja) * | 2003-01-28 | 2004-08-19 | Wakayama Prefecture | スチレン誘導体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE112005000464T5 (de) | 2007-02-15 |
| TW200600493A (en) | 2006-01-01 |
| WO2005097719A1 (en) | 2005-10-20 |
| JP2007530548A (ja) | 2007-11-01 |
| US20050228191A1 (en) | 2005-10-13 |
| US7586013B2 (en) | 2009-09-08 |
| CN1934061A (zh) | 2007-03-21 |
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