化学学报 ›› 1962, Vol. 28 ›› Issue (3): 160-166. 上一篇    下一篇

论文

2甲基-3-羥甲基-5-硝基酚的合成

李述文, 高怡生   

  1. 中国科学院药物研究所
  • 修回日期:1961-11-24 发布日期:2013-06-03

SYNTHESIS OF 2-METHYL-3-HYDROXYMETHYL-5-NITROPHENOL

LI SHU-WEN, KAO YEE-SHENG   

  1. Institute of Materia Medica, Academia Sinica
  • Revised:1961-11-24 Published:2013-06-03

1.从2一甲基-5-硝基氯化苄(Ⅵ)合成2-甲基-3羟甲基-5-硝基酚(Ⅴ)。此化合物对肉瘤180无抑制作用。2.以铬酸氧化乙酸(2-甲基-5-硝基)苄酣(Ⅺ)时,得2-甲基-5-硝基苯甲醛(ⅩⅥ)甲基未氧化而取代的甲基氧化为醛基。

In the present investigation 2-methyl-3-hydroxymethyl-5-nitrophenol (Ⅴ), which may be regarded as a ring analogue of deoxypyridoxine, was synthesized for the purpose of casting its antagonistic action against pyridoxine activity and inhibiting action on the growth of tumours.The starting material was 2-methyl-5-nitrobenzyl chloride (Ⅵ).It was nitrated to give 2-methyl-3,5-dinitrobenzyl chloride (Ⅶ), which on acet5lation was converted to 2-methyl-3,5-dinitrobenzyl acetate (Ⅷ).The latter was reduced with stannous chloride in a mixed solvent of alcohol and acetic acid to yield 2-methyl-3-amino-5-nitrobenzyl acetate (Ⅹ), which was then diazotized and hydrolysed to give the desired product (Ⅴ).In order to establish the position of the amino group, compound Ⅹ was subjected to deamination and then converted to 2-metyl-5-nitrobenzyl alcohol (ⅩⅠ).The latter gave no depression of melting point when admixed with an authentic sample prepared from Ⅵ.An attempt to convert the methyl group of V into an aldehyde group by oxidating ⅩⅡ with chromic acid resulted in the oxidation of the methylene insteaU of the methyl group of ⅩⅡ.