CAPRONITRILE, a-ETHYL

Calcium carbide, 32, 70 Calcium carbonate, 32, 81 Calcium formate, 31,102 CAPROIC ACID, e-AMINO, 32, 13 e-Caprolactam, 31, 72 32, 15 e-CAPROLACTIM, O-METHYL-, 31, 72 CAPRONITRILE, a-ETHYL, 32, 6S Caproyl chloride, 31, 71 CARBANILINONITRILE, O-CHLORO, 31, 19... 

This method is suitable for the preparation of mono- and di-a-substituted /3-ketoesters. Bromoacetates fail in this reaction. Yields with ethyl a-bromopropionate are considerably lower (30-36% with capronitrile) however, ethyl esters are useful for higher-molecular-weight compounds whose sec-alkyl esters are cracked by distillation. With 3-pentyl a-bromopropionate, the yields are slightly higher (53-60% with capronitrile). Both aromatic and aliphatic nitriles are suitable benzonitrile gives yields comparable to those obtained with capronitrile. Alkyl substitution in the a- and /8-positions (cf. Note 4) of aliphatic nitriles lowers the yield to 29% and 38%), respectively 7-substitution has no effect. 

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