Process for producing 4-hydroxycyclopentenones

Details Process for producing 4-hydroxycyclopentenones Process for producing 4-hydroxycyclopentenones

1980-05-20

1983-02-01

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568341, 568347, 568315, 568316, 568348, C07C 4529, C07C 4545, C07C 4559, C07C 4567

Patent

active

043717110

ABSTRACT:
A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atoms, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.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, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is a defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula,

REFERENCES:
patent: 3775492 (1973-11-01), Kierstead et al.
patent: 3931327 (1976-01-01), Stricker et al.
patent: 3932510 (1976-01-01), Muller et al.
patent: 3981920 (1976-09-01), Buchi
Peancatelli et al, Tetrahedron, vol. 35, pp. 135-138 (1979).
Kharasch et al., "Grignard Reactions of Nonmetallic Substances," pp. 138-144 (1954); Prentice-Hall, Inc.

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