Synthesize 2,5-diphenyl furan from ethyl benzoate and ethyl acetate

Question

claisen schimdht condensation

Answer 1

Paal-Knorr synthesis of furans:

requires 1,4-diketones:

the diphenyl-1,4-diketone [1,4-Diphenyl-1,4-butanedione] =

Ph-C=O-CH2-CH2-C=O-Ph.

prepared from the hydrodehalogenation of PhCOCHClPh, which can be made from Ethyl benzoylactetate.

Ethyl benzoylactetate can be prepared from ethyl benzoate and ethyl acetoacetate.

Answer 2

Okay here is one possibility.

Condense ethyl acetate and ethyl benzoate, then saponify and decarboxylate half of the ethyl benzoylacetate to give acetophenone.  Now brominate the acetophenone to give alpha-bromoacetophenone.  React this with the other half of the ethyl benzoylacetate to give PhC(=O)CH(COOEt)CH2C(=O)Ph.  Now saponify and decarboxylate this to give PhC(=O)CH2CH2C(=O)Ph.  Treat this with HCl and the enol will ring-close to a hemiketal and eliminate one equivalent of water.  

Voila.