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EP0022162A1
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Process for producing disubstituted 4-hydroxycyclopentenones; monosubstituted cyclopentendiones and 4-hydroxycyclopentenones
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1980-05-21
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Granted: —
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Expires: 2000-05-21
Abstract
Abstract A method of producing a 4-hydroxycyclopentenone rep resented by the formula, wherein R, is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a furylcarbinol compound of the formula, wherein R, is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, wherein R is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula. wherein R, is as defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula, R 2 MgX wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the cyclopentenone compound in the presence of a base. The 4-hydroxycyclopentenones are useful intermediates of agricultural chemicals.
Inventors
- 👤 Kenji Saito
- 👤 Hiroschi Yamachika
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 16:33
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07C; C07C45/00; C07C45/27; C07C45/29; C07C45/292; C07C45/298; C07C45/30; C07C45/56; C07C45/57; C07C45/59; C07C45/61; C07C45/67; C07C45/68; C07C49/00; C07C49/587; C07C49/597; C07C49/613; C07C49/647; C07C49/657; C07C49/683; C07C49/703; C07C49/707; C07C49/743; C07C49/747
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
107 words
A method of producing a 4-hyàroxycyclopentenone represented by the formula, wherein R 1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a cyclopentendione compound of the formula, wherein R, is as defined above, with a Grignard reagent of the formula, wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the oxocyclopentene compound in the presence of a base.
Claim 2
Independent Claim
107 words
A method of producing a 4-hyàroxycyclopentenone represented by the formula, wherein R 1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a cyclopentendione compound of the formula, wherein R, is as defined above, with a Grignard reagent of the formula, wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the oxocyclopentene compound in the presence of a base.
Claim 3
Independent Claim
134 words
A method of producing a 4-hydroxycyclopentenone represented by the formula, wherein R 1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a cyclopentenone compound of the formula, wherein R 1 is as defined above, in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, wherein R. is as defined above; reacting the cyclo- penLendione compound with a Grignard reagent of the formula, wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the oxocyclopentene compound in the presence of a base.
Claim 4
Independent Claim
134 words
A method of producing a 4-hydroxycyclopentenone represented by the formula, wherein R 1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a cyclopentenone compound of the formula, wherein R 1 is as defined above, in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, wherein R. is as defined above; reacting the cyclo- penLendione compound with a Grignard reagent of the formula, wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the oxocyclopentene compound in the presence of a base.
Claim 5
Independent Claim
169 words
A method of producing a 4-hydroxycyclopentenone represented by the formula, wherein R l is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a furylcarbinol compound of the formula, wherein R 1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, wherein R 1 is as defined above; reacting the cyclopentenone compound in the presnece of an oxidizing agent to obtain a cyclopentendione compound of the formula, wherein R 1 is as defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula, wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the oxocyclopentene compound in the presence of a base.
Claim 6
Independent Claim
169 words
A method of producing a 4-hydroxycyclopentenone represented by the formula, wherein R l is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R 2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a furylcarbinol compound of the formula, wherein R 1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, wherein R 1 is as defined above; reacting the cyclopentenone compound in the presnece of an oxidizing agent to obtain a cyclopentendione compound of the formula, wherein R 1 is as defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula, wherein R 2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined above; and reacting the oxocyclopentene compound in the presence of a base.
Claim 7
Dependent Claim
66 words
The method of producing a 4-hydroxycyclopentenone according to Claim 1, wherein the oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined in Claim 1, is produced by reacting the cyclopentendione compound of the formula, wherein R 1 is as defined in Claim 1, with a Grignard reagent of the formula, wherein R 2 and X are as defined in Claim 1.
Claim 8
Dependent Claim
95 words
The method of producing a 4-hydroxycyclopentenone according to Claim 2, wherein the oxocyclopentene compound of the formula, wherein R 1 and R 2 are as defined in Claim 2, is produced by reacting the cyclopentenone compound of the formula, wherein R 1 is as defined in Claim 2, in the presence of the oxidizing agent to obtain a cyclopentendione compound of the formula, wherein R 1 is as defined in Claim 2; and reacting the cyclopentendione compound with a Grignard reagent of the formula, wherein R 2 and X are as defined in Claim 2.
Claim 9
Dependent Claim
133 words
The method of producing a 4-hydroxycyclopentenone according to Claim 3, wherein the oxocyclo pentene compound of the formula, wherein R 1 and R 2 are as defined in Claim 3, is produced by reacting the furylcarbinol compound of the formula, wherein R 1 is as defined in Claim 3, in the presence of an acid in a mixed solvent of water and the organic solvent, to obtain the cyclopentenone compound of the formula, wherein R 1 is as defined in Claim 3; reaching the cyclopentenone compound in the presence of an oxidizing agent to obtain the cyclopentendione compound of the formula, wherein R 1 is as defined in Claim 3; and reacting the cyclopentendione compound with the Grignard reagent of the formula wherein R 2 and X are as defined in Claim 3.
Claim 10
Dependent Claim
44 words
The method of producing a 4-hydroxycyclopentenone according to Claim 2, wherein the cyclopentendione compound of the formula, wherein R, is as defined in Claim 2, is produced by oxidizing the cyclopentenone compound of the formula, wherein R 1 is as defined in Claim 2.
Claim 11
Dependent Claim
22 words
A cyclopentendione compound represented by the formula, wherein R 1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group.
Claim 12
Dependent Claim
22 words
A cyclopentendione compound represented by the formula, wherein R 1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group.
Claim 13
Dependent Claim
12 words
The cyclopentendione compound according to Claim 8, wherein R 1 is allyl.
Claim 14
Dependent Claim
21 words
A cyclopentenone compound represented by the formula, wherein R 1 is an alkenyl or alkynyl having 5 or less carbon atom.
Claim 15
Dependent Claim
21 words
A cyclopentenone compound represented by the formula, wherein R 1 is an alkenyl or alkynyl having 5 or less carbon atom.
Claim 16
Dependent Claim
12 words
The cyclopentenone compound according to Claim 10, wherein R 1 is allyl.
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