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Products of the reaction of 3-halo- and 3-ethoxypropionic acids with 1,3-dimethoxybenzene (4) in polyphosphoric acid have been shown to be 2′,4′-dimethoxy-3-(2,4-dimethoxyphenyl)-propiophenone (6) and 1,5-bis[3-(2,4-dimethoxyphenyl)-3-keto-propyl]-2,4-dimethoxybenzene (15) and these have been prepared by unambiguous syntheses. 2′,4′-Dimethoxy-3-ethoxypropiophenone (3a) and 2′,3,4′-trimethoxypropiophenone (3d) have been synthesized by the reaction of 3-chloro-2′,4′-dimethoxy- propiophenone (3c) with ethanol and methanol respectively.

Hydroxy-des-A-androst-9-en-5-one (II, R=OH), prepared from trans-1,B-hydroxy-8-methyl-4, 5-(3'-methyl-4'-methoxybenzo)-hydrindane (I, R=CH a )', has been converted into dl-9(II)-dehydrotestosterone (IV, R = OH) and dl-testosterone (IX) in very short sequences of steps, albeit in poor yields.

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