Method for producing ether compound

Patent metadata

Field	Value
Publication number	US-9975831-B2
Application number	US-201314376988-A
Country	US
Kind code	B2
Filing date	Feb 5, 2013
Priority date	Feb 9, 2012
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

An object of the present invention is to provide a method for producing an ether compound easily in a small number of steps at lower costs in high yields.
The present invention relates to a method in which the ether compound represented by the general formula (1) is produced by reacting the specific carbonyl compound specified in the general formula (2) and the specific dialkoxy compound specified in the general formula (3) with hydrogen in the presence of a hydrogenation catalyst and an acidic substance to perform hydrogenation.

First claim

The invention claimed is:

1. A method for producing an ether compound represented by the following general formula (1) through one step, which is a step of reacting a carbonyl compound represented by the following general formula (2) and a dialkoxy compound represented by the following general formula (3) with hydrogen in the presence of a hydrogenation catalyst and an acidic substance to perform hydrogenation:

wherein R 1 is an alkyl group having 1 to 20 carbon atoms which may have a substituent, a 3- to 8-membered alicyclic group which may have a substituent, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, or an aralkyl group which may have a substituent;
R 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, a 3- to 8-membered alicyclic group which may have a substituent, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, or an aralkyl group which may have a substituent; and
R 1 and R 2 may be combined to form a ring,

wherein R 3 is an alkyl group having 1 to 20 carbon atoms which may have a substituent, a 3- to 8-membered alicyclic group which may have a substituent, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, or an aralkyl group which may have a substituent provided that a group which is eliminated by hydrogenation is excluded;
R 4 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, a 3- to 8-membered alicyclic group which may have a substituent, an aryl group which may have a substituent, a heterocyclic group which may have a substituent, or an aralkyl group which may have a substituent;
R 5 is a group represented by —OR 3 ;
and further R 4 and R 5 may be combined to form a ring,

wherein definitions of R 1 to R 3 have the same meanings as described above, and
wherein an alcohol represented by the following general formula (4) is used in combination as an additional component:
R 3 OH  (4)

wherein a definition of R 3 has the same meaning as described above; and
wherein:
the mixing ratio of the carbonyl compound to the dialkoxy compound is 1 mole: 1.1-5.0 moles;
the acidic substance is at least one selected from the group consisting of benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonicacid, camphorsulfonic acid, sulfuric acid, trifluoroacetic acid, ferric chloride, zinc chloride, stannic chloride, and zinc bromide;
the hydrogenation catalyst is a heterogeneous hydrogenation catalyst containing at least one metal selected from the group consisting of palladium, iridium, rhodium, ruthenium, nickel and osmium;
a ratio of the acidic substance to the carbonyl compound (acidic substance/carbonyl compound) is in a range of 0.0030 to 0.05 in terms of weight; and
a ratio of the heterogeneous hydrogenation catalyst to the carbonyl compound (heterogeneous hydrogenation catalyst/carbonyl compound) is in a range of 0.1 to 5% by weight.

2. The production method according to claim 1 , wherein the carbonyl compound is selected from the group consisting of vanillin, 2-phenylacetaldehyde, 3,3,5-trimethylcyclohexanone, raspberry ketone, and camphor.

3. The production method according to claim 1 , wherein the mixing ratio of the carbonyl compound to the dialkoxy compound is 1 mole: 4-5 moles.

Assignees

• Takasago Perfumery Co Ltd

Inventors

• Komatsuki Yasuhiro
• Ishida Kenya
• Yagi Kenji

Classifications

• C07C43/23

  containing hydroxy or O-metal groups · CPC title

• C07C43/115

  containing carbocyclic rings · CPC title

• C07C43/1783

  with hydroxy or -O-metal groups bound to the aromatic rings · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• C07C2601/12

  with a six-membered ring · CPC title