Showing papers by "Osaka Institute of Technology published in 1971"

Synthesis of 1-Methyl-4-methoxy-7-isopropylnaphthalene

Abstract: 1-Methyl-4-methoxy-7-isopropylnaphthalene, 4-methoxy derivative of eudalene, was synthesized from p-cresol. 2-Bromo-4-methylanisole (2) was converted to 2- isopropyl-4- (2-methoxy-5-methylphenyl) butyric acid (9) through ethyl 2-cyano-2-isopropyl-4- (2-methoxy-5-methylphenyl) butyrate (5). The acid chloride of (9) was cyclized with SnCl4 to 2-isopropyl-5-methoxy-8-methyl-1, 2, 3, 4-tetrahydronaphthalen-1-one (10). As isopropyl group was attached at the α-position of the carbonyl group, 2, 4-dinitrophenylhydrazone derivative of (10) was yielded with difficulty. 1-Methyl-4-methoxy-7-isopropylnaphthalene (12) was obtained by reduction of (10) and then heating the product with sulfur.