6-hydroxy-3-hexenyl alkoxymethyl ether compound and a process for preparing a 3,13-octadecadien-1-ol compound from the same

Patent metadata

Field	Value
Publication number	US-11661394-B2
Application number	US-202117489908-A
Country	US
Kind code	B2
Filing date	Sep 30, 2021
Priority date	Oct 2, 2020
Publication date	May 30, 2023
Grant date	May 30, 2023

Abstract

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH═CHCH2CH2OCH2OCH2R′ (1), R1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH3(CH2)3CH═CH(CH2)8CH═CHCH2CH2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

First claim

The invention claimed is:

1. A process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6):
CH 3 (CH 2 ) 3 CH═CH(CH 2 ) 8 CH═CHCH 2 CH 2 OH  (6),

the process comprising:
halogenating a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1):
HOCH 2 CH 2 CH═CHCH 2 CH 2 OCH 2 OCH 2 R 1   (1)

wherein R 1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group
to prepare a 6-halo-3-hexenyl alkoxymethyl ether compound of the following general formula (2):
X 1 CH 2 CH 2 CH═CHCH 2 CH 2 OCH 2 OCH 2 R 1   (2)

wherein X 1 represents a halogen atom, and R 1 is as defined above;
converting the 6-halo-3-hexenyl alkoxymethyl ether compound (2) into a nucleophilic reagent, 6-(alkoxymethoxy)-3-hexenyl compound of the following general formula (3):
MCH 2 CH 2 CH═CHCH 2 CH 2 OCH 2 OCH 2 R 1   (3)

wherein M represents Li, MgZ 2 , CuZ 2 , or CuLiZ 2 , wherein Z 2 represents a halogen atom or a 6-(alkoxymethoxy)-3-hexenyl group, and R 1 is as defined above;
subjecting the nucleophilic reagent, 6-(alkoxymethoxy)-3-hexenyl compound (3), to a coupling reaction with a 12-halo-5-dodecene of the following general formula (4):
CH 3 (CH 2 ) 3 CH═CH(CH 2 ) 6 X 2   (4)

wherein X 2 represents a halogen atom,
to prepare a 3,13-octadecadiene alkoxymethyl ether compound of the following general formula (5):
CH 3 (CH 2 ) 3 CH═CH(CH 2 ) 8 CH═CHCH 2 CH 2 OCH 2 OCH 2 R 1   (5)

wherein R 1 is as defined above; and
dealkoxymethylating the 3,13-octadecadiene alkoxymethyl ether compound (5) to prepare the 3,13-octadecadien-1-ol compound (6).

2. A process for preparing a 3,13-octadecadienyl acetate compound of the following formula (7):
CH 3 (CH 2 ) 3 CH═CH(CH 2 ) 8 CH═CHCH 2 CH 2 OAc  (7)

wherein Ac represents an acetyl group,
the process comprising:
the process according to claim 1 for preparing the 3,13-octadecadien-1-ol compound (6), and
acetylating the resulting 3,13-octadecadien-1-ol compound (6) to prepare the 3,13-octadecadienyl acetate compound (7).

Assignees

• Shinetsu Chemical Co

Inventors

• Miyake Yuki
• Kinsho Takeshi
• Nagae Yusuke

Classifications

• C07C67/08 Primary

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

• C07C41/24

  by elimination of halogens, e.g. elimination of HCl · CPC title

• C07F3/02

  Magnesium compounds · CPC title

• C07C29/128

  by alcoholysis · CPC title

• C07C41/22

  by introduction of halogens; by substitution of halogen atoms by other halogen atoms · CPC title