N-butyrophenones

The elimination of C2H4 from n-butyrophenones (117) has been found to yield a rough correlation with the Hammett a values for the substitu-... 

Eldridge (1982a,b) reported analysis of soybean and soy products using HPLC with an external standard method. They found 80% ethanol extraction for 4 hr was suitable for extraction of isoflavones from soybean, soy protein concentrate and protein isolate. They also found that daidzin and genistin accounted for 50-75% of the total isoflavones. Eldridge and Kwolek (1983) reported analysis using selected external standards and n-butyrophenone as an internal standard. 

Unfortunately the condensation failed with certain a-halo ketones, for example -bromoacetone. Successful alkylation of this ketone would provide a useful route to methyl ketones. Brown et al.4 then explored use of a number of other bases the most satisfactory proved to be 2,6-di-/-butyl phenoxide. This is a weak base and a-haloketones are stable in its presence for a considerable length of time. The presence of the bulky alkyl substituents also appears to be highly favorable. Thus the following yields of n-butyrophenone were obtained from the reaction of phenacyl bromide and triethylborane with the bases indicated potassium phenoxide (2%), potassium 2-methylphenoxide (29%), potassium 2,6-dimethylphenoxide (75%), and potassium 2,6-di-f-butylphenoxide (98%). 

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