1,8-CINEOLE-9-SUBSTITUTED COMPOUND AND PRODUCTION THEREOF

摘要

NEW MATERIAL:The 1,8-cineole-9-substituted compound of formula III (A is H or 1-4C acyl). EXAMPLE:9-Acetoxy-1,8-cineole. USE:An intermediate for herbicide, agricultural chemicals (repellent for pine weevil), etc. PREPARATION:The objective compound of formula III can be produced in high yield in two steps comprising (1) oxidation of 1,8-methadiene of formula I [easily available from 2-pinene or 2(10)-pinene which are main components of turpentine oil available at a low cost] with lead tetroxide in a mixed solvent comprising glacial acetic acid and acetic anhydride, etc., to produce 1-p-menthene glycol monoacetate of formula II and (2) intramolecular cyclization of the product under thermal refluxing in a solvent such as hexane in the presence of an acidic bisulfate such as acidic potassium bisulfate preferably for 2-8hr under stirring.