Method for producing 5, 5-disubstituted-4, 5-dihydroisoxazole

Patent metadata

Field	Value
Publication number	US-10975041-B2
Application number	US-201816954082-A
Country	US
Kind code	B2
Filing date	Dec 13, 2018
Priority date	Dec 15, 2017
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

The present invention addresses the problem of providing an industrially preferable, economical, and environmentally friendly method for producing the 4,5-dihydroisoxazole represented by a formula (3).

The present invention enables the compound of a formula (3) to be produced by reacting the compound of a formula (2) according to the reaction represented by a reaction formula in the presence of an acid catalyst.

First claim

The invention claimed is:

1. A process for producing a compound of the formula (3):

wherein R 1 and R 2 are each independently a (C1-C4)alkyl,
which comprises the following step:
step (B): reacting a compound of the formula (2) in the presence of an acid catalyst to produce the compound of the formula (3),

wherein R 1 and R 2 are as defined above.

2. The process according to claim 1 , wherein the compound of the formula (2) is produced by a process comprising the following step (A),
step (A): reacting a compound of the formula (1) with an oximating agent to produce the compound of the formula (2),

wherein, R 1 and R 2 are as defined above.

3. The process according to claim 2 , wherein the oximating agent in the step (A) is hydroxylamine or a salt thereof.

4. The process according to claim 2 , wherein the oximating agent in the step (A) is hydroxylamine, hydroxylamine hydrochloride or hydroxylamine sulfate.

5. The process according to claim 2 , wherein the reaction of the step (A) is performed in the presence of a base.

6. The process according to claim 5 , wherein the base in the step (A) is sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or ammonia.

7. The process according to claim 2 , wherein the reaction of the step (A) is performed in the presence of one or more solvents selected from water, acetonitrile, toluene, xylene, chlorobenzene, dichlorobenzene and dichloromethane.

8. The process according to claim 2 , wherein the reaction of the step (A) is performed in the presence of a solvent composed of a combination of water and dichlorobenzene.

9. The process according to claim 1 , wherein the acid catalyst in the step (B) is one or more acid catalysts selected from the group consisting of mineral acids, carboxylic acids, sulfonic acids, phosphoric acids and Lewis acids.

10. The process according to claim 1 , wherein the acid catalyst in the step (B) is one or more acid catalysts selected from the group consisting of nitric acid, trifluoroacetic acid, trichloroacetic acid, maleic acid, maleic anhydride, benzenesulfonic acid and p-toluenesulfonic acid.

11. The process according to claim 1 , wherein the acid catalyst in the step (B) is trifluoroacetic acid or maleic acid.

12. The process according to claim 1 , wherein the reaction of the step (B) is performed in the presence of 0.1 to 0.5 equivalents of a base catalyst based on 1 equivalent of the acid catalyst.

13. The process according to claim 12 , wherein the base catalyst in the step (B) is N-methylaniline, morpholine or pyrrolidine.

14. The process according to claim 1 , wherein the reaction of the step (B) is performed in the presence of one or more solvents selected from water, acetonitrile, toluene, xylene, chlorobenzene, dichlorobenzene and dichloromethane.

15. The process according to claim 1 , wherein the reaction of the step (B) is performed in the presence of dichlorobenzene solvent.

16. The process according to claim 1 , wherein the compound of the formula (2) is 3-methyl-2-butenal oxime, and the compound of the formula (3) is 5,5-dimethyl-4,5-dihydroisoxazole.

17. The process according to claim 7 , wherein the acid catalyst in the step (B) is one or more acid catalysts selected from the group consisting of nitric acid, trifluoroacetic acid, trichloroacetic acid, maleic acid, maleic anhydride, benzenesulfonic acid and p-toluenesulfonic acid.

18. The process according to claim 7 , wherein the reaction of the step (B) is performed in the presence of one or more solvents selected from water, acetonitrile, toluene, xylene, chlorobenzene, dichlorobenzene and dichloromethane.

19. The process according to claim 7 , wherein the compound of the formula (2) is 3-methyl-2-butenal oxime, and the compound of the formula (3) is 5,5-dimethyl-4,5-dihydroisoxazole.

20. The process according to claim 17 , wherein the compound of the formula (2) is 3-methyl-2-butenal oxime, and the compound of the formula (3) is 5,5-dimethyl-4,5-dihydroisoxazole.

Assignees

• Kumiai Chemical Industry Co

Inventors

• Nagata Toshihiro

Classifications

• C07D261/04 Primary

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• C07C251/40

  to carbon atoms of an unsaturated carbon skeleton · CPC title

• C07C249/08 Primary

  by reaction of hydroxylamines with carbonyl compounds · CPC title

• C07B61/00

  Other general methods · CPC title

• B01J31/04

  containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)} · CPC title