Mt. Bachute et Rb. Mane, SYNTHESIS OF AN INTERMEDIATE, 7,8-DIMETHYL-2-TETRALONE, FOR OCCIDOL ISOMER-I AND OCCIDOL ISOMER-II, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 37(3), 1998, pp. 281-284
Anisole is succinoylated with succinic anhydride to yield 3-(p-methoxy
benzoyl) propionic acid 3. The acid on Clemmensen reduction gives 4-(p
-methoxy phenyl) butyric acid 4 which on esterification affords methyl
4-(p-methoxyphenyl)butyrate 5. The ester 5 on reaction with methylmag
nesium iodide gives 5-(p-methoxyphenyl)-2-methylpentan-2-ol 6 which is
cyclised with PPA to furnish 7-methoxy-1,1-dimethyltetralin 7. The te
tralin 7 undergoes aromatization with p-chloranil or DDQ to afford 7-m
ethoxy1,2-dimethyl naphthalene 8, the reduction of which with sodium i
n liquid ammonia as well as with sodium in ethanol yields 7,8-dimethyl
-2-tetralone 10.