反应详情

It is well known that beta-isophorone can be oxidized by air using noble metal catalysts (FR-A 2 335 486). In addition to 4-ketoisophorone and alpha-isophorone, the desired 4-hydroxyisophorone is obtained in this reaction as a byproduct also. 4-Hydroxyisophorone can also be obtained directly from alpha-isophorone in small yields using a biochemical method with Aspergillus niger (JP-OS 81 35 990; Y. Mikami et al., Agric. Biol. Chem. 1981, 45, 791-3). A. Heymes and P. Teisseire obtained 4-hydroxyisophorone in 34% yield by oxidation with monoperphthalic acid (Recherches 1971, 18, 104-8), while N. S. Zarghami and D. E. Heinz (Phytochemistry 1971, 10, 2755-61) disclosed no yield information for the reaction with peracetic acid. J. N. Marx and F. Sondheimer report a yield of 87% from the treatment of beta-isophorone with m-chloroperbenzoic acid, but the recalculation of the results they reported shows only a yield of 56%, which is also in agreement with other information in the literature (Tetrahedron, Suppl. No. 8, Pt. 1, 1-7, 1966; see also O. Isler et al., Helv. Chim. Acta 39, 2041, 1956).