Synthesis of substituted 3 ',4 '-dihyrospiro[indane-1,2 '(1 ' H) naphthalene]-1 '-ols and their catalytic dehydrogenation

Catalytic dehydrogenation of 5',7'-dimethyl-3',4'-dihydrospiro[indane-1, 2' (1'H) naphthalene]-1'-ol 5a, 7'-ethyl-3',4'-dihydrospiro[indane-1, 2'-(1'H) naphthalene]-1'-ol 5b, 6-methyl-3', 4'-dihydrospiro[indane-1, 2'(1'H) naph thalene]-1'-ol 5c and 6, 7'-dimethyl-3', 4'-dihydrospiro[indane-1, 2'(1'H) naphthalene]-1'-ol 5d affords 1,3-dimethylchrysene 6a, a mixture of 3-ethyl chrysene 6b and chrysene, 3-methylchrysene 6c and 3, 9-dimethylchrysene 6d , respectively. condensation of anhydride of 1a of 1-carboxyindane-1-acetic acid with m-xylene and ethylbenzene give ketoacids 2a and 2b while 2c and 2d are obtained by condensation of the anhydride 1b of 1-carboxy-6-methylin dane-1-acetic acid with benzene and toluene respectively. Catalytic reducti on in acetic acid solution of 2a, 2c, 2d, and in ethanolic solution of 2b, give 3a, 3c, 3d and 3b. In ethanolic solution, 2c and 2d give esters 3c(E) and 3d(E). Intramolecular acylation of 3a, 3b, 3c and 3c(E) and 3d and 3d(E ) give 4a, 4b, 4c and 4d which after LAH reduction followed by dehydrogenat ion gave chrysenes 6a, 6b, 6c and 6d. Structures of all compounds corrobora te their spectral data.