WO2008099882A1 - ２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナール及びその製造方法 - Google Patents

２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナール及びその製造方法 Download PDF

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Publication number
WO2008099882A1
WO2008099882A1 PCT/JP2008/052442 JP2008052442W WO2008099882A1 WO 2008099882 A1 WO2008099882 A1 WO 2008099882A1 JP 2008052442 W JP2008052442 W JP 2008052442W WO 2008099882 A1 WO2008099882 A1 WO 2008099882A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
methylenedioxyphenyl
reaction mixture
propanal
methylenedioxybenzene
Prior art date
Application number
PCT/JP2008/052442
Other languages
English (en)
French (fr)
Inventor
Takashi Doi
Yoshihiro Yoshida
Eiji Sajiki
Satoru Fujitsu
Original Assignee
Ube Industries, Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ube Industries, Ltd. filed Critical Ube Industries, Ltd.
Priority to US12/526,697 priority Critical patent/US8168809B2/en
Priority to JP2008558119A priority patent/JP5446272B2/ja
Priority to CN200880004697.2A priority patent/CN101605774B/zh
Priority to EP20080711284 priority patent/EP2119713B1/en
Publication of WO2008099882A1 publication Critical patent/WO2008099882A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

　（１）１，２－メチレンジオキシベンゼン及び２－メチル－３，３－ジアセトキシプロペンを反応させる方法、又は１，２－メチレンジオキシベンゼン、メタクロレイン及び無水酢酸を反応させる方法により、１－アセトキシ－２－メチル－３－（３，４－メチレンジオキシフェニル）－１－プロペンを含む反応混合物を得た後、これを加水分解反応又はアルコールとのエステル交換反応に付して、２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナールを含む粗生成物を得た後、該反応混合物を蒸留精製する方法であって、特定の操作により該反応混合物中の高沸点化合物を除去する２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナールの製造方法、及び（２）その方法により得られる、酢酸含有量が４０ｐｐｍ未満である、香料として有用な高純度の２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナールである。
PCT/JP2008/052442 2007-02-15 2008-02-14 ２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナール及びその製造方法 WO2008099882A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US12/526,697 US8168809B2 (en) 2007-02-15 2008-02-14 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, and method for production thereof
JP2008558119A JP5446272B2 (ja) 2007-02-15 2008-02-14 ２−メチル−３−（３，４−メチレンジオキシフェニル）プロパナール及びその製造方法
CN200880004697.2A CN101605774B (zh) 2007-02-15 2008-02-14 2-甲基-3-（3,4-亚甲二氧苯基）丙醛及其制造方法
EP20080711284 EP2119713B1 (en) 2007-02-15 2008-02-14 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, and method for production thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007034177 2007-02-15
JP2007-034177 2007-02-15

Publications (1)

Publication Number Publication Date
WO2008099882A1 true WO2008099882A1 (ja) 2008-08-21

Family

ID=39690109

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/052442 WO2008099882A1 (ja) 2007-02-15 2008-02-14 ２－メチル－３－（３，４－メチレンジオキシフェニル）プロパナール及びその製造方法

Country Status (6)

Country Link
US (1) US8168809B2 (ja)
EP (2) EP2119713B1 (ja)
JP (1) JP5446272B2 (ja)
CN (1) CN101605774B (ja)
TW (1) TWI422581B (ja)
WO (1) WO2008099882A1 (ja)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101622238B (zh) 2007-03-07 2013-05-29 宇部兴产株式会社 2-甲基-3-（3,4-亚甲二氧基苯基）丙醛的品质保持方法及其制备方法
CA2756362C (en) 2010-12-22 2018-07-31 Sulzer Chemtech Ag Method of mass transfer, structured packing and mass transfer apparatus for a small liquid load
CN103304536B (zh) * 2013-06-13 2014-12-17 安徽华业香料股份有限公司 高含量新洋茉莉醛的制备方法
CN104650027B (zh) * 2014-12-24 2018-04-06 成都建中香料香精有限公司 一种新洋茉莉醛的合成工艺
CN104650028A (zh) * 2014-12-24 2015-05-27 成都建中香料香精有限公司 一种新洋茉莉醛单酯的合成工艺
CN113527077A (zh) * 2020-04-16 2021-10-22 成都三香汇香料有限公司 一种苯甲醚制取茴香基丙醛的方法
CN113501804A (zh) * 2021-05-24 2021-10-15 兄弟科技股份有限公司 一种新洋茉莉醛的合成方法
CN115894222A (zh) * 2023-01-18 2023-04-04 潍坊三力本诺化学工业有限公司 一种2-甲基烯丙基二乙酸酯的合成及提纯方法

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB841921A (en) * 1958-02-11 1960-07-20 Polak & Schwarz Internationaal 2-piperonyl-propanal, a new perfume, and process for making same
US3008968A (en) 1958-02-11 1961-11-14 Int Flavors & Fragrances Inc Process for making 2-methyl-3-(3'-4'-methylenedioxyphenyl)-propanal
JPS55141437A (en) 1979-04-20 1980-11-05 Toray Ind Inc Preparation of alkenylcarboxylate derivative
JPS5745124A (en) 1980-07-04 1982-03-13 Givaudan & Cie Sa Manufacture of dihydrocinnamyl aldehyde derivative
JPS61151152A (ja) 1984-12-24 1986-07-09 Mitsubishi Rayon Co Ltd アルケニリデンジアセテ−トの製造法
JPH10120674A (ja) * 1996-10-24 1998-05-12 T Hasegawa Co Ltd ２−メチル−３−（３，４−メチレンジオキシフェニル）アクリルアルデヒドの製法
WO2004054997A1 (ja) 2002-12-18 2004-07-01 Ube Industries, Ltd. １−アセトキシ−３−（置換フェニル）プロペン化合物の製造方法
JP2004269376A (ja) * 2003-03-06 2004-09-30 Ube Ind Ltd １−ホルミル−３−（３，４−メチレンジオキシフェニル）プロペン誘導体の製法
JP2005239620A (ja) * 2004-02-26 2005-09-08 Ube Ind Ltd １−アセトキシ−３−（３，４−メチレンジオキシフェニル）プロペン誘導体の製法
JP2005239619A (ja) 2004-02-26 2005-09-08 Ube Ind Ltd １−アセトキシ−２，３−ジ置換−プロペン化合物の製造法
JP2006104151A (ja) 2004-10-07 2006-04-20 Ube Ind Ltd ３−ベンゾ［１，３］ジオキソール−５−イル−２−メチルプロピオンアルデヒドの製造法
WO2006120639A2 (en) 2005-05-11 2006-11-16 Firmenich Sa Catalytic scriabine reaction

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100336811C (zh) * 2002-12-18 2007-09-12 宇部兴产株式会社 1－乙酰氧基－3－(取代苯基)丙烯化合物的制备方法

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB841921A (en) * 1958-02-11 1960-07-20 Polak & Schwarz Internationaal 2-piperonyl-propanal, a new perfume, and process for making same
US3008968A (en) 1958-02-11 1961-11-14 Int Flavors & Fragrances Inc Process for making 2-methyl-3-(3'-4'-methylenedioxyphenyl)-propanal
JPS55141437A (en) 1979-04-20 1980-11-05 Toray Ind Inc Preparation of alkenylcarboxylate derivative
JPS5745124A (en) 1980-07-04 1982-03-13 Givaudan & Cie Sa Manufacture of dihydrocinnamyl aldehyde derivative
JPS61151152A (ja) 1984-12-24 1986-07-09 Mitsubishi Rayon Co Ltd アルケニリデンジアセテ−トの製造法
JPH10120674A (ja) * 1996-10-24 1998-05-12 T Hasegawa Co Ltd ２−メチル−３−（３，４−メチレンジオキシフェニル）アクリルアルデヒドの製法
WO2004054997A1 (ja) 2002-12-18 2004-07-01 Ube Industries, Ltd. １−アセトキシ−３−（置換フェニル）プロペン化合物の製造方法
JP2004269376A (ja) * 2003-03-06 2004-09-30 Ube Ind Ltd １−ホルミル−３−（３，４−メチレンジオキシフェニル）プロペン誘導体の製法
JP2005239620A (ja) * 2004-02-26 2005-09-08 Ube Ind Ltd １−アセトキシ−３−（３，４−メチレンジオキシフェニル）プロペン誘導体の製法
JP2005239619A (ja) 2004-02-26 2005-09-08 Ube Ind Ltd １−アセトキシ−２，３−ジ置換−プロペン化合物の製造法
JP2006104151A (ja) 2004-10-07 2006-04-20 Ube Ind Ltd ３−ベンゾ［１，３］ジオキソール−５−イル−２−メチルプロピオンアルデヒドの製造法
WO2006120639A2 (en) 2005-05-11 2006-11-16 Firmenich Sa Catalytic scriabine reaction

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ANGEW. CHEM. INT. ED., vol. 39, no. 17, 2000, pages 2980
See also references of EP2119713A4

Also Published As

Publication number Publication date
EP2119713A4 (en) 2011-05-04
EP2562173B1 (en) 2016-02-10
TW200906815A (en) 2009-02-16
JP5446272B2 (ja) 2014-03-19
US20100121085A1 (en) 2010-05-13
US8168809B2 (en) 2012-05-01
EP2119713B1 (en) 2015-04-29
JPWO2008099882A1 (ja) 2010-05-27
EP2119713A1 (en) 2009-11-18
EP2562173A1 (en) 2013-02-27
CN101605774B (zh) 2013-05-29
TWI422581B (zh) 2014-01-11
CN101605774A (zh) 2009-12-16

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