Synthesis of 5-Methylresorcinol Orcinol

Methylmagnesium bromide (35 g) was added to 1,3-dimethoxy-5-benzoyl chloride (100 g) to obtain 1,3-dimethoxy-methylphenone in a jdeld of 45%. Then, the reduction was conducted by adding water (300 cc), concentrated hydrochloric acid (300 cc) and 1,3-dimethoxy-methylphenone (100 g) to zinc amalgam obtained from zinc (400 g) and mercuric chloride (20 g). Further, concentrated hydrochloric acid (10 to 15 cc) was added every one hour. After the completion of the reaction, the reaction solution was cooled and saturated with sodium 

As hereinbefore pointed out, the 5-(tertiary alkyl)resorcinols thus prepared in accordance with this invention are important intermediates in the preparation of useful drugs. For example, 5-(l,l-dimethyl-heptyl)resorcinol is utilized in the preparation of l-hydroxy-3-(l,l-dimethylheptyl)-6,6a,7,8,9,l 0,10a-hexahydro-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one, which compound is extremely useful in the treatment of depression in humans, as described in U.S. Pat. Nos. 3,928,598, 3,944,673, and 3,953,603. Similarly, 5-(l,l-dimethyl-heptyl)resorcinol is required in the synthesis of3-(l,l-dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-6H-dibenzo[b,d]pyran-l,9-diol, which compound is useful as a blood-pressure lowering agent. It can thus be seen that a commercially feasible process for preparing 5-(tertiary alkyl)resorcinols in high yield is desirable. 

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