Aromatic musks derived from 1,2,3,4-tetrahydro-1,1,4,4,6,7-hexamethylnaphthalene

Abstract

Bromination of the title hydrocarbon gave the 6,7-bis(bromomethyl) compound (2), base-catalysed condensation of which with active methylene compounds gave a series of musks having the 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethylbenz[f]indene skeleton (3) with various functional groups at C-2. Treatment of the dibromide (2) with sodium hydroxide or with sodium sulphide formed the cyclic ether (5a) and sulphide (5b), respectively, the latter being oxidised to the sulphoxide and sulphone. Further bromination produced the tetrabromide (8) which was hydrolysed to the dialdehyde (9), the starting point for a further series of musks. The two strongest musks were the methyl ester (3g) and the naphthofuran (5a).