Methods for producing β-cyclolavandulal and derivative of same

US9708241B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-9708241-B2
Application numberUS-201415021168-A
CountryUS
Kind codeB2
Filing dateSep 11, 2014
Priority dateSep 12, 2013
Publication dateJul 18, 2017
Grant dateJul 18, 2017

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Abstract

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Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to obtain a 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether compound (2) and hydrolyzing Compound (2) to obtain the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde (3); a method for producing (2,4,4-trimethyl-1-cyclohexene)methanol, comprising a step of reducing Compound (3) to obtain the (2,4,4-trimethyl-1-cyclohexene)methanol (4); and a method for producing a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound, comprising a step of esterifying Compound (4) to obtain the (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound (5).

First claim

Opening claim text (preview).

The invention claimed is: 1. A method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting a carbonyl group of 2,4,4-trimethyl-2-cyclohexenone of Formula (1): with a triphenylphosphonium alkoxymethylide of formula (C 6 H 5 ) 3 P═CHOR 1 , wherein R 1 is a monovalent hydrocarbon group having 1 to 8 carbon atoms, to obtain a 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether compound of General Formula (2): wherein R 1 is as recited above; and hydrolyzing the 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether to obtain the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde of Formula (3): 2. A method for producing (2,4,4-trimethyl-1-cyclohexene)methanol, comprising: the steps comprised by the method according to claim 1 to obtain the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde; and a step of reducing the (2,4,4-trimethyl-1-cyclohexene)carbaldehyde to obtain the (2,4,4-trimethyl-1-cyclohexene)methanol of Formula (4): 3. A method for producing a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound, comprising: the steps comprised by the method according to claim 2 to obtain the (2,4,4-trimethyl-1-cyclohexene)methanol; and a step of esterifying the (2,4,4-trimethyl-1-cyclohexene)methanol with a compound selected from the group consisting of an acylating agent, a carboxylic acid, and a carboxylic ester to obtain the (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound represented byof General Formula (5): wherein R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms.

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What does patent US9708241B2 cover?
Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to obtain a 2,4,4-trimethyl-2-cyclohexenylidenemethyl ether compound (2) and hydrolyzing Compound (2) to obtain the (2,4,4-trimethyl-1-…
Who is the assignee on this patent?
Shinetsu Chemical Co
What technology area does this patent fall under?
Primary CPC classification C07C29/14. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Jul 18 2017 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).