The chemistry of some methoxychlor derivatives

Abstract
The preparation of 1-chloro-2,2-bis(p-methoxyphenyl)ethylene (3a) and of 1-chloro-2,2-bis(p-hydroxyphenyl)ethylene (3b), required for a study of the microbial degradation of methoxychlor (1a) was reinvestigated. The methoxy compound (3a) was readily obtained by alkaline dehydrohalogenation of 1,1-dichloro-2,2-bis(p-methoxyphenyl)ethane (2a), but similar treatment of 1,1-dichloro-2,2-bis(p-hydroxyphenyl)ethane (2b) gave a chlorine-free compound, characterized as the diethyl acetal of 2,2-bis(p-hydroxyphenylacetaldehyde (5a) on the basis of spectroscopic evidence and comparison with a model compound. Also, 2,2-bis(p-methoxyphenyl)acetic acid (4a) and 2,2-bis(p-hydroxyphenyl)acetic acid (4b) were prepared and the solubility and p-values (ethyl acetate/water) of these acids were determined.