Substituted octalinones and tetrahydro-indanones of use as intermediates in steroid synthesis

975,594. Substituted octalinones and tetrahydroindanones. H. SMITH. Dec. 20, 1960 [Sept. 25, 1959(2); Feb. 19, 1960], Nos. 40557/60, 40558/60 and 40559/60. Divided out of 975,593. Heading C2C. The invention comprises compounds of formula wherein Ar is phenyl which may be substituted in the m-position with hydroxy, alkoxy, acyloxy, nitro, amino, acylamino or alkylamino as sole substituent, each R is H or alkyl, R <SP>1</SP> is alkyl, Q is methylene or ethylene, and Y is carbonyl, ketalised carbonyl, hydroxymethylene or acyloxymethylene. The compounds and those in which Ar is more generally phenyl having an unsubstituted ortho-position may be prepared by one of the following methods: (a) (Y=carbonyl) cyclodehydration of a compound of formula (b) (Y=carbonyl) condensation of a compound ArCR 2 CR 2 X (X=Cl, Br or organic sulphonyloxy) with a metal enolate of a ketone of structure. (c) (Y=hydroxymethylene) selective reduction of the corresponding compound wherein Y is carbonyl and (d) (Y=ketalised carbonyl or acyloxymethylene) respectively ketalising or esterifying the corresponding compound wherein Y is carbonyl or hydroxymethylene. In examples, the preparation is described of compounds wherein (1)-(12) Ar is phenyl or m-methoxyphenyl, R<SP>1</SP> is methyl, Y is carbonyl, hydroxymethylene or ethylenedioxymethylene and Q is methylene or ethylene; (13), (14), (16), (17) Ar is m-nitro- or m-aminophenyl, R <SP>1</SP> is methyl, Y is carbonyl or hydroxymethylene and Q is methylene, the amino compounds being obtained by reduction of corresponding nitro compounds; (15), (18) Ar is m-acetaminophenyl, R<SP>1</SP> is methyl, Y is carbonyl or acetoxymethylene by acetylation of the appropriate amino precursors. Specifications 975,591, 975,592, 975,595 and 975,596 also are referred to.