Propyl phenyl ketone

When the cyclic component is benzene or naphthalene, the -ic acid or -oic acid of the acid corresponding to the acyl group is changed to -ophenone or -onaphthone, respectively. For example, C5H5—CO—CH2CH2CH3 can be named either butyrophenone (or butanophenone) or phenyl propyl ketone. 

Phenyl-2-propenoic acid, e279 3-Phenyl-2-propen-l-ol, c282 3-Phenyl-2-propenoyl chloride, c280 3-Phenylpropyl alcohol, pi46 Phenyl propyl ketone, b619... 

Although similar efforts have been devoted to related polymer systems (Overberger and Cho, 1968 Overberger and Dixon, 1977 Okamoto, 1978), large enantioselectivity has not been observed. Goldberg et al. (1978) conducted borohydride reduction of phenyl ketones in micelles of the chiral surfactant [44]. The result was disappointing, since the maximal enantioselectivity was only 1.66% for phenyl propyl ketone. A much better optical yield was reported when this reaction was carried out under phase-transfer conditions (Masse and Parayre, 1976). The cholic acid micelle and bovine serum albumin exhibited the relatively high enantioselectivity in the reduction of trifluoroacetophenone (Baba ef al., 1978). 

Experiment 6.121 BUTYROPHENONE (Phenyl propyl ketone-use of the acyl chloride)... 

C H,Br 0, [4-Brom-phenylJ-Cy-broni-/J.nitio.y.phenyl-propyl]-keton 7 I 241. 

Phenyl-[ -phenyl-propyl]-keton-phenyl hydnzon 16,149. 

Aromatic ketones are often named by treating the benzene ring as a phenyl group, as in isopropyl phenyl ketone (Fig. 16.12). A few can be named through the lUPAC system in which the framework Ph—C=0 is indicated by the term ophenone and the remainder of the molecule designated by one of the alternative names in Rgure 16.12. Thus, diphenyl ketone is benzophenone, methyl phenyl ketone is acetophenone, ethyl phenyl ketone is propiophenone, and phenyl propyl ketone is butyrophenone (Fig. 16.12). 

Phenyl propyl ketone (butyrophenone) TM 4.3b is available by common Friedel-Crafts acylation. On the other hand, ferfbutyl propyl ketone TM 4.4a is not an easily available Cg building block. Butanoic acid is produced by either fermentation of starch using the Bacillus subtilis strain or oxidation of n-butanal, available by formylation of propene (Scheme 4.3). 

FIGURE 16.25 NMR spectrum of phenyl propyl ketone, C5H5COC3H7. 

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