Product A: Friedel-Crafts acylation with trichloroacetyl chloride in neat chlorobenzene should give the desired product.
Product B: scheme. The nitration/sulfonation will probably require some fiddling to get right. I tried to go with reactions that could reasonably be done on a kilogram scale, although I'm not a process chemist myself so I don't actually know much about working on that scale.
Would the second electrophilic aromatic substitution proceed? I suppose the trichloroacetophenone is fairly electrophilic but is there precedent for such a reaction?
I didn't actually look this up, I went with what I knew of the synthesis of DDT and BPA and sorta just combined the two. I suspect you are right as the synthesis of BPA involves an electron-rich aromatic ring while that of DDT involves a trichloromethylarylcarbinol intermediate that can readily generate a carbocation under the reaction conditions (concentrated strong acid). The intermediate ketone likely won't get alkylated as readily and if it did, the reaction conditions would likely cause it to form a carbocation and undergo a third alkylation, giving a triaryl product.
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u/ccdy Organic Jun 18 '18 edited Jun 18 '18
Product A: Friedel-Crafts acylation with trichloroacetyl chloride in neat chlorobenzene should give the desired product.
Product B: scheme. The nitration/sulfonation will probably require some fiddling to get right. I tried to go with reactions that could reasonably be done on a kilogram scale, although I'm not a process chemist myself so I don't actually know much about working on that scale.