8-(acyloxy)alkanal compound, process for preparing the same and process for preparing 2,9-diacetoxyundecane from the 8-(acyloxy)alkanal compound

Patent metadata

Field	Value
Publication number	US-2025084028-A1
Application number	US-202418826468-A
Country	US
Kind code	A1
Filing date	Sep 6, 2024
Priority date	Sep 7, 2023
Publication date	Mar 13, 2025
Grant date	—

Abstract

The present invention provides an 8-(acyloxy)alkanal compound (1), wherein n represents 0 or 1, and R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom, and a process for preparing the same. The process comprises the steps of subjecting the aforesaid 8-(acyloxy)alkanal compound (1) to a nucleophilic addition reaction with a nucleophilic reagent, alkyl compound (2), wherein M 1 represents Li, MgZ 1 , CuZ 1 , or CuLiZ 1 , n represents 0 or 1, and Z 1 represents a halogen atom, a methyl group, or an ethyl group, to form 2,9-undecanediol (3), and subjecting the 2,9-undecanediol (3) to an acetylation reaction to form the 2,9-diacetoxyundecane (4).

First claim

1 . An 8-(acyloxy)alkanal compound of the following general formula (1):

wherein n represents 0 or 1, and R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom.

2 . A process for preparing 2,9-diacetoxyundecane of the following formula (4):

the process comprising the steps of
subjecting an 8-(acyloxy)alkanal compound of the following general formula (1):

wherein n represents 0 or 1, and R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom,
to a nucleophilic addition reaction with a nucleophilic reagent, alkyl compound, of the following general formula (2):
CH 3 (CH 2 ) (1−n) M 1   (2)

wherein M 1 represents Li, MgZ 1 , CuZ 1 , or CuLiZ 1 , n represents 0 or 1, and Z 1 represents a halogen atom, a methyl group, or an ethyl group,
to form 2,9-undecanediol of the following formula (3):

and subjecting the 2,9-undecanediol (3) to an acetylation reaction to form the aforesaid 2,9-diacetoxyundecane (4).

3 . A process for preparing an 8-(acyloxy)alkanal compound of the following general formula (1):

wherein n represents 0 or 1, and R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom,
the process comprising the step of
subjecting a dialkoxyacyloxyalkane compound of the following general formula (5):

wherein n represents 0 or 1, R 1 is as defined above, and R 3 and R 4 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms; or R 3 and R 4 form together a divalent hydrocarbon group, R 3 —R 4 , having 2 to 10 carbon atoms,
to a hydrolysis reaction to form the aforesaid 8-(acyloxy)alkanal compound (1).

4 . The process for preparing the 8-(acyloxy)alkanal compound (1) according to claim 3 , with proviso that n is 0,
the process comprising the steps of
converting a 6-halo-1,1-dialkoxyhexane compound of the following general formula (6):

wherein X represents a halogen atom, and R 3 and R 4 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms; or R 3 and R 4 form together a divalent hydrocarbon group, R 3 —R 4 , having 2 to 10 carbon atoms,
into a nucleophilic reagent, 6,6-dialkoxyhexyl compound, of the following general formula (7):

wherein M 2 represents Li, MgZ 2 , CuZ 2 , or CuLiZ 2 , Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group, and R 3 and R 4 are as defined above,
subsequently subjecting the nucleophilic reagent, 6,6-dialkoxyhexyl compound (7), to a nucleophilic addition reaction with propylene oxide of the following formula (8):

to form a 9,9-dialkoxy-2-nonanol compound of the following general formula (9A):

wherein R 3 and R 4 are as defined above,
subjecting the 9,9-dialkoxy-2-nonanol compound (9A) to acylation to form the dialkoxyacyloxyalkane compound (5) as defined in claim 3 with proviso that n is 0;
and the process according to claim 3 for preparing the 8-(acyloxy)alkanal compound (1) as defined in claim 3 , with proviso that n is 0, by subjecting the aforesaid dialkoxyacyloxyalkane compound (5) as defined in claim 3 with proviso that n is 0, to a hydrolysis reaction.

5 . The process for preparing the 8-(acyloxy)alkanal compound (1) according to claim 3 , with proviso that n is 1,
the process comprising the steps of converting a 6-halo-1,1-dialkoxyhexane compound of the following general formula (6):

wherein X represents a halogen atom, and R 3 and R 4 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms; or R 3 and R 4 form together a divalent hydrocarbon group, R 3 —R 4 , having 2 to 10 carbon atoms,
into a nucleophilic reagent, 6,6-dialkoxyhexyl compound, of the following general formula (7):

wherein M 2 represents Li, MgZ 2 , CuZ 2 , or CuLiZ 2 , Z 2 represents a halogen atom or a 6,6-dialkoxyhexyl group, and R 3 and R 4 are as defined above,
subsequently subjecting the nucleophilic reagent, 6,6-dialkoxyhexyl compound (7), to a nucleophilic addition reaction with 1,2-butylene oxide of the following formula (10):

to form a 10,10-dialkoxy-3-decanol compound of the following general formula (9B):

wherein R 3 and R 4 are as defined above,
subjecting the 10,10-dialkoxy-3-decanol (9B) to acylation to form the dialkoxyacyloxyalkane compound (5) as defined in claim 3 with proviso that n is 1;
and the process according to claim 3 for preparing the 8-(acyloxy)alkanal compound (1) as defined in claim 3 , with proviso that n=1, by subjecting the dialkoxyacyloxyalkane compound (5) as defined in claim 3 with proviso that n is 1 to a hydrolysis reaction.

6 . The process for preparing 2,9-diacetoxyundecane (4) according to claim 2 , further comprising:
preparing the 8-(acyloxy)alkanal compound of the following general formula (1):

wherein n represents 0 or 1, and R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom,
the process for preparing the 8-(acyloxy)alkanal compound (1) comprising subjecting a dialkoxyacyloxyalkane compound of the following general formula (5):

wherein n represents 0 or 1, R 1 is as defined above, and R 3 and R 4 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms; or R 3 and R 4 form together a divalent hydrocarbon group, R 3 —R 4 , having 2 to 10 carbon atoms,
to a hydrolysis reaction to form the 8-(acyloxy)alkanal compound (1).

7 . The process for preparing 2,9-diacetoxyundecane (4) as according to claim 2 , further comprising
converting a 6-halo-1,1-dialkoxyhex

Assignees

• Shinetsu Chemical Co

Inventors

• Miyake Yuki
• Watanabe Takeru
• Komatsu Ryo

Classifications

• C07C69/78

  Benzoic acid esters · CPC title

• C07C69/18

  of trihydroxylic compounds · CPC title

• C07C67/293

  by isomerisation; by change of size of the carbon skeleton · CPC title

• C07F3/02

  Magnesium compounds · CPC title

• C07C69/16

  of dihydroxylic compounds · CPC title