Title:
METHOD FOR PRODUCING CYCLOHEXENONE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2022/176837
Kind Code:
A1
Abstract:
A method for producing a cyclohexenone compound that includes an isomerization step that brings a reaction raw material including a compound represented by formula (4) into contact with an isomerization catalyst in a solvent to obtain a compound represented by formula (3). Preferably, the following steps are carried out in order: an addition step for reacting a compound (1) with methyl vinyl ketone in a solvent in the presence of a base to obtain a compound (2); a cyclization step for reacting the compound (2) in a solvent in the presence of a strong acid to obtain a compound (3); and an isomerization step for bringing a compound (4) included as an impurity in the reaction product obtained by the cyclization step into contact with an isomerization catalyst in a solvent.
Inventors:
NAGAHAMA MASAKI (JP)
TANIIKE HIROTSUGU (JP)
INOUE JUN (JP)
TANIIKE HIROTSUGU (JP)
INOUE JUN (JP)
Application Number:
PCT/JP2022/005854
Publication Date:
August 25, 2022
Filing Date:
February 15, 2022
Export Citation:
Assignee:
API CORP (JP)
International Classes:
C07C45/67; B01J27/13; B01J31/22; C07C45/65; C07C49/603; C07C67/313; C07C69/716; C07B61/00
Domestic Patent References:
| WO2018038265A1 | 2018-03-01 |
Foreign References:
| JPS5610121A | 1981-02-02 | |||
| JP2021025335A | 2021-02-22 |
Other References:
PRAKASH, G.K.S. TONGCO, E.C. MATHEW, T. VANKAR, Y.D. OLAH, G.A.: "Preparation of 3-trifluoromethyl-2-cycloalkenones by the oxidative rearrangement of trifluoromethylated tertiary allylic alcohols with pyridinium chlorochromate", JOURNAL OF FLUORINE CHEMISTRY, vol. 101, no. 2, 1 February 2000 (2000-02-01), NL , pages 199 - 202, XP004244518, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(99)00159-1
SHEN RUICHAO, COREY E. J.: "Studies of the Stereochemistry of [2+2]-Photocycloaddition Reactions of 2-Cyclohexenones with Olefins", ORGANIC LETTERS, vol. 9, no. 6, 1 March 2007 (2007-03-01), US , pages 1057 - 1059, XP055961024, ISSN: 1523-7060, DOI: 10.1021/ol063092r
JEAN-PIERRE BÉGUÉ,DANIÈLE BONNET-DELPON &ANUKWADEY DOGBEAVOU: "Efficient Procedure to 4-Carbethoxy-3-Trifluoro Methylcyclohex-2-Enone and 4-Alkylated Derivatives", SYNTHETIC COMMUNICATIONS, vol. 22, no. 4, 1 January 1992 (1992-01-01), US , pages 573 - 579, XP009539164, ISSN: 0039-7911, DOI: 10.1080/00397919208019256
LEGROS, J. BARHOUMI-SLIMI, T. CROUSSE, B. BONNET-DELPON, D. EL GAIED, M. BEGUE, J.-P.: "Regioselective alkylation of the trifluoromethyl analog of Hagemann's ester", JOURNAL OF FLUORINE CHEMISTRY, vol. 108, no. 1, 1 March 2001 (2001-03-01), NL , pages 91 - 94, XP004231226, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(01)00344-X
J. FLUORINE. CHEM., vol. 101, 2000, pages 199 - 202
SYNTHETIC COMMUN, vol. 22, no. 4, 1992, pages 573 - 579
ANGEW. CHEM. INT. ED., vol. 53, 2014, pages 2628 - 2632
J. CHEM. SOC., PERKIN TRANS., vol. 1, 1977, pages 359 - 363
SHEN RUICHAO, COREY E. J.: "Studies of the Stereochemistry of [2+2]-Photocycloaddition Reactions of 2-Cyclohexenones with Olefins", ORGANIC LETTERS, vol. 9, no. 6, 1 March 2007 (2007-03-01), US , pages 1057 - 1059, XP055961024, ISSN: 1523-7060, DOI: 10.1021/ol063092r
JEAN-PIERRE BÉGUÉ,DANIÈLE BONNET-DELPON &ANUKWADEY DOGBEAVOU: "Efficient Procedure to 4-Carbethoxy-3-Trifluoro Methylcyclohex-2-Enone and 4-Alkylated Derivatives", SYNTHETIC COMMUNICATIONS, vol. 22, no. 4, 1 January 1992 (1992-01-01), US , pages 573 - 579, XP009539164, ISSN: 0039-7911, DOI: 10.1080/00397919208019256
LEGROS, J. BARHOUMI-SLIMI, T. CROUSSE, B. BONNET-DELPON, D. EL GAIED, M. BEGUE, J.-P.: "Regioselective alkylation of the trifluoromethyl analog of Hagemann's ester", JOURNAL OF FLUORINE CHEMISTRY, vol. 108, no. 1, 1 March 2001 (2001-03-01), NL , pages 91 - 94, XP004231226, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(01)00344-X
J. FLUORINE. CHEM., vol. 101, 2000, pages 199 - 202
SYNTHETIC COMMUN, vol. 22, no. 4, 1992, pages 573 - 579
ANGEW. CHEM. INT. ED., vol. 53, 2014, pages 2628 - 2632
J. CHEM. SOC., PERKIN TRANS., vol. 1, 1977, pages 359 - 363
Attorney, Agent or Firm:
SHIGENO, Tsuyoshi et al. (JP)
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