The Reaction of Nucleophilic Addition of Acetonitrile to Substituted Benzaldehydes Using t-BuOK as a Catalyst

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Other Title
  • カリウムt-ブトキシド触媒によるアセトニトリルの置換ベンズアルデヒドへの求核付加反応

Description

The reaction of acetonitrile with p-anisaldehyde was studied in detail. In EtOH, the protic polar solvent, no reaction occurred, but in such aprotic polar solvents as DMF, HMPA or THF the reaction rapidly proceeded to give 2-cyano-1- (4-methoxyphenyl) -1-hydroxyethane 12 c13 and 4-methoxycinnamic nitrile 1113 cli in the total yield of 87- 95%. The yields of 1112 c13 and 13 c13 were found to be remarkably influenced by the reaction temperature and solvent.<BR>Furthermore, a prolonged treatment of acetonitrile with substituted benzaldehydes 11 all-. -fill eli under similar conditions was found to give I -hydroxy-I3-phenylpropionitrile derivatives 111213 or cinnamic nitrile derivatives 11313. The yields of 1211 and 1311 were influenced by the substituents. It was found that as electron-repelling character of the substituent, except in the case of 2, 4-dimethoxybenzaldehyde 11 dli, increased, the yield of 1213 decreased and the yield of 1313 increased.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (12), 2347-2350, 1973-12-10

    The Chemical Society of Japan

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