GB397212A - Improvements in the manufacture of optically active menthols - Google Patents

Improvements in the manufacture of optically active menthols

Info

Publication number
GB397212A
GB397212A GB656732A GB656732A GB397212A GB 397212 A GB397212 A GB 397212A GB 656732 A GB656732 A GB 656732A GB 656732 A GB656732 A GB 656732A GB 397212 A GB397212 A GB 397212A
Authority
GB
United Kingdom
Prior art keywords
menthol
ester
chloride
optically
acid
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.)
Expired
Application number
GB656732A
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.)
WILLIAM JOHN GRUBB
Tronox Pigment UK Ltd
Original Assignee
WILLIAM JOHN GRUBB
Cristal Pigment UK 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 WILLIAM JOHN GRUBB, Cristal Pigment UK Ltd filed Critical WILLIAM JOHN GRUBB
Priority to GB656732A priority Critical patent/GB397212A/en
Publication of GB397212A publication Critical patent/GB397212A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C07C35/12—Menthol

Abstract

A mixture of d- and l-menthols is resolved into its optically-active components by esterification with d- or l-menthoxyacetic acid, isolating one of the esters by fractional crystallization and hydrolysing it under such conditions that the liberated menthoxyacetic acid is not decomposed. For the hydrolysis, treatment with a slight excess of dilute alcoholic alkali solution is suitable. The esterification is preferably effected with the use of the optically-active menthoxyacetyl chloride, prepared by treatment of the acid with thionyl chloride, in the presence of a tertiary base such as pyridine or quinoline. According to the examples, racemic menthol is esterified with l-menthoxyacetyl chloride and d-menthol obtained from the ester which crystallizes out from methyl alcohol; the ester remaining in the mother liquor is saponified, the recovered menthol esterified with d-menthoxyacetyl chloride, and l-menthol isolated by hydrolysis of the ester after its crystallization from methyl alcohol.
GB656732A 1932-03-04 1932-03-04 Improvements in the manufacture of optically active menthols Expired GB397212A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB656732A GB397212A (en) 1932-03-04 1932-03-04 Improvements in the manufacture of optically active menthols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB656732A GB397212A (en) 1932-03-04 1932-03-04 Improvements in the manufacture of optically active menthols

Publications (1)

Publication Number Publication Date
GB397212A true GB397212A (en) 1933-08-24

Family

ID=9816850

Family Applications (1)

Application Number Title Priority Date Filing Date
GB656732A Expired GB397212A (en) 1932-03-04 1932-03-04 Improvements in the manufacture of optically active menthols

Country Status (1)

Country Link
GB (1) GB397212A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3171855A (en) * 1962-02-12 1965-03-02 Glidden Co Separating isomeric menthyl oxalate esters by agitating a crystallizing mixture of said esters
US3943181A (en) * 1971-02-27 1976-03-09 Haarmann & Reimer Gesellschaft Mit Beschrankter Haftung Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol
US8785698B2 (en) 2009-02-17 2014-07-22 Nagaoka & Co., Ltd. Methods and apparatus for production of natural L-menthol
CN104829422A (en) * 2015-04-10 2015-08-12 湖南利洁生物化工有限公司 Method for splitting D,L-menthol

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3171855A (en) * 1962-02-12 1965-03-02 Glidden Co Separating isomeric menthyl oxalate esters by agitating a crystallizing mixture of said esters
US3943181A (en) * 1971-02-27 1976-03-09 Haarmann & Reimer Gesellschaft Mit Beschrankter Haftung Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol
US8785698B2 (en) 2009-02-17 2014-07-22 Nagaoka & Co., Ltd. Methods and apparatus for production of natural L-menthol
CN104829422A (en) * 2015-04-10 2015-08-12 湖南利洁生物化工有限公司 Method for splitting D,L-menthol

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