K. Adachi
Feb 1, 1973
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0
Influential Citations
1
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Journal
Journal of Synthetic Organic Chemistry Japan
Abstract
1-Methyl-3-methoxy-7-isopropylnaphthalene, the 3-methoxy derivative of eudalene, was synthesized from m-cresol. The Grignard reagent of 4-bromo-3-methylanisole (1) was converted to give 3- (4-methoxy-2-methylphenyl) succinic acid (4), which was dehydrated with P2O5 to give the acid anhydride (5). The Friedel-Crafts reaction of (5) using AlCl3 yielded 7-methoxy-5-methyl-1-oxo-1, 2, 3, 4-tetrahydronaphthalene-3-carboxylic acid (6). 6-Methoxy-8-methyl-2- (1-hydroxy-1-methylethyl) -1, 2, 3, 4-tetrahydronaphthalene (9), obtained by the reduction followed by the methylation of (6), yielded 1-methyl-3-methoxy-7-isopropylnaphthalene (10) along with the thiophene derivative (12) by heating with sulfur. The demethylation of (10) afforded 4-methyl-6-isopropyl-2-naphthol (11).