7-methyl-3-methylene-7-octenal acetal compound and methods for producing aldehyde compound and ester compound using the same

Patent metadata

Field	Value
Publication number	US-10611718-B2
Application number	US-201715825299-A
Country	US
Kind code	B2
Filing date	Nov 29, 2017
Priority date	Dec 7, 2016
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4).

First claim

The invention claimed is:

1. A method for simultaneously producing a 7-methyl-3-methylene-7-octenyl carboxylate compound of General Formula (4):

wherein R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, and

a 3,7-dimethyl-2,7-octadienyl carboxylate compound of General Formula (7):

wherein R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms,

the method comprising steps of:
subjecting a 7-methyl-3-methylene-7-octenal acetal compound of General Formula (1):

wherein R 1 and R 2 , which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms,

to hydrolysis and isomerization to obtain a first mixture of 7-methyl-3-methylene-7-octenal of Formula (2):

and
3,7-dimethyl-2,7-octadienal of Formula (5):

wherein an acid or a base is present in the isomerization;
reducing the first mixture to obtain a second mixture of 7-methyl-3-methylene-7-octenol of Formula (3):

and
3,7-dimethyl-2,7-octadienol of Formula (6):

and
esterifying the second mixture to obtain a third mixture of the 7-methyl-3-methylene-7-octenyl carboxylate compound (4) and the 3,7-dimethyl-2,7-octadienyl carboxylate compound (7).

Assignees

• Shinetsu Chemical Co

Inventors

• Kinsho Takeshi
• Baba Akihiro
• Nagae Yusuke
• Watanabe Tomohiro

Classifications

• C07C29/14

  of a —CHO group · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C45/42 Primary

  by hydrolysis · CPC title

• C07C67/14

  from carboxylic acid halides · CPC title

• C07D317/12

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title