PRODUCTION OF 3,4-CARANEDIOL

摘要

PURPOSE: To obtain 3,4-caranediol useful as a repellent for insect pests, by reacting 3-carene with an organic hydroperoxide and then reacting the reaction product with an alkali metal. CONSTITUTION: 3-Carene of formula I is reacted with an organic hydroperoxide (e.g. tert-butyl hydroperoxide) in the presence of a hydrocarbon-soluble molybdenum salt in a solvent (e.g. toluene) at 50-100 deg.C to give 3 caraneepoxide of formula II. Then the compound of formula II is reacted with an alkali metal hydroxide or an alkali metal carbonate under 5-15kg/cm<2> in hydrous ethanol at 100-200 deg.C to give 3,4-caranediol of formula III. The hydrocarbon-soluble molybdenum salt is obtained by heating ammonium molybdate with a 4-30C hydrocarboncarboxylic acid in the presence of an organic amine under heating.