Menthofuran → 7a-Hydroxy-3,6-dimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one

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Reaction Steps

The chemical structure of (6R)-4,5,6,7-tetrahydro-3,6-dimethyl-3H-benzo [b]furan-2-one is known. In fact, K. Schulte-Elte et al in Tetrahedron (1967), 23(6), 2583-2599 identified the compound of the formula (I) in a mixture of lactones resulting from the photooxidation of menthofuran. Furthermore, J. Hirsch et al in J. Org. Chem. (1967), 32(9), 2915-2916 also identified the lactone (I) from among other end products resulting from the hydrolysis of α,α′-dimethoxydihydromenthofuran. However, these authors specify that the lactone (I) oxidises very easily under the synthesis conditions described to give a hydroxylactone, 5,6,7,7a-tetrahydro-7a-hydroxy-3,6-dimethyl-4H-benzo[b]furan-2-one of the formula

Provenance & Evidence