9-蒽羧酸类化合物的合成

SYNTHESIS OF 9-ANTHRACENECARBOXYLIC ACIDS

9-蒽羧酸类化合物由于具有特殊的光、电性质,因而在实验室和工业上有重要的用途。本文首次应用不同的相转移催化条件,包括固液相转移催化和超声波催化技术研究了9-蒽酮与丙烯腈的Michael加成反应和相继的水解反应,进而用锌和浓氨水还原羰基合成了9-蒽-β-丙酸(Ⅱ).用蒽与N-甲基甲酰苯胺反应制备了9-蒽甲醛,继而与丙二酸反应,水解、脱羧制备了9-蒽丙烯酸(Ⅰ)。由这一化合物催化加氢也可得到(Ⅱ)。

9-Anthracenecarboxylic acids are used widely in laboratories and industry. The 9-Anthraeene-β-propionic acid (Ⅱ) was synthesized by the reaction of anthrone and acrylonitrile with ultrasonic wave or tetrabutyl ammonium bromide as the phase-transfer catalyst, followed by hydrolysis and reduction using zinc and aqueous ammonia. The β-(9-Anthracene) acrylic acid(Ⅰ) was prepared by the reaction of 9-anthraldehyde and malonic acid,and decarboxylation. The compound (Ⅱ) was also prepared by catalytic hydrogenation of the compound(Ⅰ).