A process for preparing 5-isopropylidene-2,7- dihydroxy-9-substituted-2,6- methano-3,4,5,6- tetrahydro-2H-1-benzoxocins of the formula IMAGE in which R1 is C5-C10 alkyl, C5-C10 alkenyl, C5-C8 cycloalkyl, or C5-C8 cycloalkenyl; which process is characterized by reacting a 1-alkoxy-4-(1- hydroxy-1-methylethyl)-1, 4-cyclohexadiene of the formula IMAGE wherein R3 is C1-C4 alkyl, with a 5-substituted resorcinol of the formula IMAGE in an organic solvent in the presence of stannic chloride for from 1 to 15 minutes at a temperature from -40 DEG C. to ambient temperature. The benzoxocins prepared are useful intermediates in the production of dibenzo [b,d] pyran-9- ores which are anti-anxiety, analgesic and anti-depressant drugs.
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