Processes for preparing 4-methyl-5-nonanone and 4-methyl-5-nonanol

Patent metadata

Field	Value
Publication number	US-10882806-B2
Application number	US-201916722138-A
Country	US
Kind code	B2
Filing date	Dec 20, 2019
Priority date	Dec 21, 2018
Publication date	Jan 5, 2021
Grant date	Jan 5, 2021

Abstract

The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3), the process comprising at least a step of subjecting pentanoic anhydride of the following formula (1) and a 2-pentyl nucleophilic reagent of the following general formula (2), in which M represents Li, MgZ 1 , or ZnZ 1 , wherein Z 1 represents a halogen atom or a 2-pentyl group, to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (7), the process comprising at least steps of preparing 4-methyl-5-nonanone and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7).

First claim

The invention claimed is:

1. A process for preparing 4-methyl-5-nonanone of the following formula (3):

the process comprising at least a step of
subjecting pentanoic anhydride of the following formula (1):

and a 2-pentyl nucleophilic reagent of the following general formula (2):
CH 3 CH 2 CH 2 CH(CH 3 )M   (2)

in which M represents Li, MgZ 1 , or ZnZ 1 , wherein Z 1 represents a halogen atom or a 2-pentyl group,
to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3).

2. The process according to claim 1 , further comprising
subjecting 2-pentanol of the following formula (4):

and a halogenating agent to a halogenation reaction to produce a 2-halopentane compound of the following general formula (5):

in which X represents a halogen atom; and
preparing the aforesaid 2-pentyl nucleophilic reagent (2) from the aforesaid 2-halopentane compound (5).

3. The process according to claim 2 , wherein the halogenating agent is a sulfonyl halide compound of the following formula (6):
XSO 2 R   (6)

in which X represents a halogen atom, wherein R represents a monovalent hydrocarbon group having from 1 to 7 carbon atoms,
and the halogenation reaction is carried out in the presence of a basic compound.

4. The process according to claim 1 , further comprising
during or after the aforesaid nucleophilic substitution reaction, recovering pentanoic acid which was by-produced in the nucleophilic substitution reaction.

5. The process according to claim 4 , further comprising subjecting the recovered pentanoic acid to a condensation reaction to produce pentanoic anhydride (1).

6. The process according to claim 5 , wherein the obtained pentanoic anhydride (1) is used in the nucleophilic substitution reaction.

7. The process according to claim 5 , further comprising repeating the nucleophilic substitution reaction with use of the obtained pentanoic anhydride (1) as a raw material for the nucleophilic substitution reaction.

8. A process for preparing 4-methyl-5-nonanol of the following formula (7):

the process comprising at least steps of
preparing 4-methyl-5-nonanone (3) according to claim 1 ; and
subjecting the obtained 4-methyl-5-nonanone (3) and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7).

9. The process according to claim 2 , further comprising during or after the aforesaid nucleophilic substitution reaction, recovering pentanoic acid which was by-produced in the nucleophilic substitution reaction.

10. The process according to claim 9 , further comprising subjecting the recovered pentanoic acid to a condensation reaction to produce pentanoic anhydride (1).

11. The process according to claim 10 , wherein the obtained pentanoic anhydride (1) is used in the nucleophilic substitution reaction.

12. The process according to claim 10 , further comprising repeating the nucleophilic substitution reaction with use of the obtained pentanoic anhydride (1) as a raw material for the nucleophilic substitution reaction.

13. The process according to claim 3 , further comprising
during or after the aforesaid nucleophilic substitution reaction, recovering pentanoic acid which was by-produced in the nucleophilic substitution reaction.

14. The process according to claim 13 , further comprising subjecting the recovered pentanoic acid to a condensation reaction to produce pentanoic anhydride (1).

15. The process according to claim 14 , wherein the obtained pentanoic anhydride (1) is used in the nucleophilic substitution reaction.

16. The process according to claim 14 , further comprising repeating the nucleophilic substitution reaction with use of the obtained pentanoic anhydride (1) as a raw material for the nucleophilic substitution reaction.

Assignees

• Shinetsu Chemical Co

Inventors

• Miyake Yuki
• Kinsho Takeshi
• Komatsu Ryo

Classifications

• C07C45/455 Primary

  with carboxylic acids or their derivatives · CPC title

• C07C51/56

  from organic acids, their salts, their esters {or their halides, e.g. by carboxylation} · CPC title

• C07F1/02

  Lithium compounds · CPC title

• C07F3/06

  Zinc compounds · CPC title

• C07C17/16 Primary

  of hydroxyl groups · CPC title