| abstract |
PURPOSE: cis-2,2,3-Trimethyl-6-methylene-cyclohexylacetaldehyde, as a starting material, is converted into a novel intermediate to give the titled trans isomer- free compound, which is used as a durative flavor or modifier. n CONSTITUTION: The compound of formula 1 is obtained inexpensively and readily from 3,3,4-trimethyl-1-cycylohexenylmethanol, then it is brought into contact with KCN in the presence of acetic acid in an organic solvent to form the compound of formula 2, which is allowed to react with mesyl chloride in the presence of a base catalyst, then with sodium selenophenoxide to give the compound of formula 3. Then, the product is allowed to react with hydrogen peroxide in the presence of a base to give (±)-cis-3-(2,2,3-trimethyl-6-methylenecyclohexy)- acrylonitrile. The product is allowed to react with methyl lithium to give the objective compound of formula B. The compounds of formulas 2 through 4 are novel and the compounds of formulas 2 and 4 have durable flower-like or citrus- like smells. n COPYRIGHT: (C)1985,JPO&Japio |