JPS5536459A - Optically active lilial and its preparation - Google Patents

Optically active lilial and its preparation

Info

Publication number
JPS5536459A
JPS5536459A JP11094378A JP11094378A JPS5536459A JP S5536459 A JPS5536459 A JP S5536459A JP 11094378 A JP11094378 A JP 11094378A JP 11094378 A JP11094378 A JP 11094378A JP S5536459 A JPS5536459 A JP S5536459A
Authority
JP
Japan
Prior art keywords
formula
optically active
tert
lilial
compound
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.)
Granted
Application number
JP11094378A
Other languages
Japanese (ja)
Other versions
JPS5848530B2 (en
Inventor
Kazuhiko Hamada
Kanji Nishizawa
Yasuo Hazama
Tadatoshi Akitani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co 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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP11094378A priority Critical patent/JPS5848530B2/en
Publication of JPS5536459A publication Critical patent/JPS5536459A/en
Publication of JPS5848530B2 publication Critical patent/JPS5848530B2/en
Expired legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

NEW MATERIAL:Optically active p-tert-butyl-α-methyldihydrocinnamaldehyde of formula I'.
USE: Synthetic aldehyde perfumes having a fragrance like a lily of the valley, particularly the (-) isomer is a perfume superior to the racemic lilial.
PROCESS: p-tert-Butyl-α-methyl-dihydrocinnamic acid of formula II is reacted with an optically active amine, e.g. α-phenyl-β-tolylethylamine, in a solvent, e.g. ethanol, at room temperature to give salts. A slightly soluble diastereomer salt is selectively crystallized, and decomposed to recover an optically active amine. The resulting compound of formula II' is then reacted with thionyl chloride to form a compound of formula III', which is reduced with LiAl(OBu-tert)3H in a solvent, e.g. THF, to give the compound of formula I'.
COPYRIGHT: (C)1980,JPO&Japio
JP11094378A 1978-09-08 1978-09-08 Method for producing optically active Lilial Expired JPS5848530B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP11094378A JPS5848530B2 (en) 1978-09-08 1978-09-08 Method for producing optically active Lilial

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP11094378A JPS5848530B2 (en) 1978-09-08 1978-09-08 Method for producing optically active Lilial

Publications (2)

Publication Number Publication Date
JPS5536459A true JPS5536459A (en) 1980-03-14
JPS5848530B2 JPS5848530B2 (en) 1983-10-28

Family

ID=14548480

Family Applications (1)

Application Number Title Priority Date Filing Date
JP11094378A Expired JPS5848530B2 (en) 1978-09-08 1978-09-08 Method for producing optically active Lilial

Country Status (1)

Country Link
JP (1) JPS5848530B2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4749815A (en) * 1986-02-14 1988-06-07 Givaudan Corporation Process for the manufacture of p-tert-butyl-alpha-methyl-hydrocinnamaldehyde
JPH03221599A (en) * 1990-01-26 1991-09-30 Takasago Internatl Corp Perfume composition
JP2008534448A (en) * 2005-03-17 2008-08-28 ビーエーエスエフ ソシエタス・ヨーロピア Process for producing optically active 3-phenylpropionic acid derivatives and subsequent products of the derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0513621Y2 (en) * 1986-02-28 1993-04-12

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4749815A (en) * 1986-02-14 1988-06-07 Givaudan Corporation Process for the manufacture of p-tert-butyl-alpha-methyl-hydrocinnamaldehyde
US4778934A (en) * 1986-02-14 1988-10-18 Givaudan Corporation Process for the manufacture of p-tert-butyl-α-methylhydrocinnamaldehyde
JPH03221599A (en) * 1990-01-26 1991-09-30 Takasago Internatl Corp Perfume composition
JP2008534448A (en) * 2005-03-17 2008-08-28 ビーエーエスエフ ソシエタス・ヨーロピア Process for producing optically active 3-phenylpropionic acid derivatives and subsequent products of the derivatives
JP4763771B2 (en) * 2005-03-17 2011-08-31 ビーエーエスエフ ソシエタス・ヨーロピア Process for producing optically active 3-phenylpropionic acid derivatives and subsequent products of the derivatives

Also Published As

Publication number Publication date
JPS5848530B2 (en) 1983-10-28

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