Process for preparing a 3,7-dimethylalkane compound

Patent metadata

Field	Value
Publication number	US-11685703-B2
Application number	US-202218058316-A
Country	US
Kind code	B2
Filing date	Nov 23, 2022
Priority date	Nov 25, 2021
Publication date	Jun 27, 2023
Grant date	Jun 27, 2023

Abstract

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M 1 represents Li, Mg Z 1 , CuZ 1 , or CuLiZ 1 , wherein Z 1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X 1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3).

First claim

The invention claimed is:

1. A process for preparing a 3,7-dimethylalkane compound of the following formula (3):

wherein n is 5 or 6,
the process comprising:
subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound, of the following general formula (1):

wherein M 1 represents Li, Mg Z 1 , CuZ 1 , or CuLiZ 1 , wherein Z 1 represents a halogen atom or a 2,6-dimethyloctyl group,
to a coupling reaction with an electrophilic alkyl reagent of the following general formula (2):

wherein X 1 represents a halogen atom or a p-toluenesulfonate group, and n is as defined above,
to form the 3,7-dimethylalkane compound (3).

2. The process for preparing a 3,7-dimethylalkane compound (3) according to claim 1 , the process further comprising:
subjecting a nucleophilic reagent, 3-methylpentyl compound, of the following general formula (4):

wherein M 2 represents Li, MgZ 2 , CuZ 2 , or CuLiZ 2 , wherein Z 2 represents a halogen atom or a 3-methylpentyl group,
to a coupling reaction with a 1,3-dihalo-2-methylpropane compound of the following general formula (5):

wherein X 2 and X 3 may be same with or different from each other and represent a halogen atom,
to form a 1-halo-2,6-dimethyloctane compound of the following formula (6):

wherein X 4 represents a halogen atom, and
preparing the nucleophilic reagent, 2,6-dimethyloctyl compound (1), from the 1-halo-2,6-dimethyloctane compound (6).

Assignees

• Shinetsu Chemical Co

Inventors

• Miyake Yuki
• Watanabe Takeru
• Kinsho Takeshi

Classifications

• C07C5/44 Primary

  with halogen or a halogen-containing compound as an acceptor · CPC title

• C07C1/325 Primary

  the hetero-atom being a metal atom · CPC title

• C07C1/326 Primary

  the hetero-atom being a magnesium atom · CPC title

• C07F3/02

  Magnesium compounds · CPC title

• C07C29/36

  increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal · CPC title