COMPOSITION OF MIXTURES OF HYDROCARBONS AFTER BIRCH-REDUCTION OF SUBSTITUTED BENZENES AND ACID-CATALYZED ADDITION OF ALCOHOLS TO ALKYLSUBSTITUTED CYCLOHEXENES AND CYCLOHEXA-1,4-DIENES

10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2. The product mixture compositions are determined through capillary GLC. On storage at + 6-degrees-C some rearomatization of the 1,4-cyclohexadienes 2 occurs. Data of the H-1- and C-13-n.m.r. spectra and also mass spectra of the BIRCH 1,4-dienes 2 are given. For comparison 4-alkoxycyclohexenes 4 and 1-alkoxy-1-methylcyclohexanes 8 are prepared and spectroscopically characterized. Acid-catalyzed addition of alcohols to the 1,4-cyclohexadiene systems is a slow process and gives the 4-alkoxy-4-alkylcyclohex-1-enes (4) only in moderate yields up to 30%. Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.