Ethyl 3-Hydroxy-3,0-diphenylpropionate

This procedure is an adaptation of ones described by Dunna-vant and Hauser.2"4 Ethyl /3-hydroxy-/3,/3-diphenylpropionate has been prepared previously using the Reformatsky reaction by condensing ethyl a-bromoacetate with benzophenone by means of zinc metal.5... 

Somewhat less than the equivalent amount of dry Na-ethoxide added with stirring and cooling at —10 to an ethereal soln. of equimolar amounts of benzophenone and ethyl fluoroacetate, after the addition stirring continued without cooling unless room temp, is exceeded ethyl -fluoro-j -hydroxy-/ , -diphenylpropionate. Y 60%.—If applicable, this method is simpler than the Reformatkii synthesis, which would require ethyl bromofluoroacetate as startg. m. F. e. with lower yields s. V. F. Martynov and M. I. Titov, 7K. 32, 718 (1962) G. A. 58, 6740a. 

Phenylcinnamic acid has been prepared previously by a variety of methods, the best of which appear to be the dehydration of ethyl j3-hydroxy-/3,(3-diphenylpropionate by treatment with sodium acetate in acetic acid6 and the reaction of 1,1-diphenylethylene with oxalyl chloride.7... 

This procedure illustrates the use of lithio esters for the preparation of /3-hydroxy esters. Isopropyl and /-butyl /3-hydroxy-/8,/3-diphenylpropionate may be prepared in approximately 80% yields by using isopropyl or /-butyl acetates in place of ethyl acetate.2 This procedure is generally more convenient than the Reformatsky reaction for the preparation of such esters. Under similar conditions ethyl acetate may conveniently be condensed with various aldehydes or ketones to give the corresponding /8-hydroxy esters.4... 

ETHYL P-HYDROXY-P.P-DIPHENYLPROPIONATE (Hydracrylic acid, 3,3-diphenyl, ethyl ester)... 

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