Butyrio acid

The ketones are readily prepared, for example, acetophenone from benzene, acetyl chloride (or acetic anhydride) and aluminium chloride by the Friedel and Crafts reaction ethyl benzyl ketones by passing a mixture of phoiylacetic acid and propionic acid over thoria at 460° and n-propyl- p-phenylethylketone by circulating a mixture of hydrocinnamic acid and n-butyrio acid over thoria (for further details, see under Aromatic Ketones, Sections IV,136, IV,137 and rv,i4i). 

Fig. 17. GLC of a mixture of indole derivatives (1 /jg of each derivative injected). For conditions see text. IAN = indole-3-acetonitrile lAA-ME = methyl ester of in-dole-3-acetic acid lAA-EE = ethylindole 3-acetate ICA-ME = methyl ester of in-dole-3-carboxylio acid IPA-ME = methyl ester of indole-3-propionic acid IBA-ME = methyl ester of indole-3-butyrio acid 6-OH-IAA-ME = 5-hydroxyindole-3-acetic acid (methyl ester). Reproduced from Brook et al. (B22) with permission.

It was found that the signs of rotation of the recovered a-phenyl-butyrio acid corresponded to the known absolute configurations of the deuteriated alcohols if and only if the size relationships CH3 > CfDs and H>D were valid. In the case of ( + )-(S)-2-propanol-l,l,l-ds (4), the optical yield was between 0-4 and 0-5% (Horeau et al., 1965), corresponding to a A AG value of about 23 cal mol at 26°C. For the primaiy alcohols, quite analogous results were obtained (Horeau and Nouaille, 1966). 

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