α-Naphthyl methyl ketoneの合成

概要

論文の詳細を見る
In the course of study of furyl ketone derivatives as contact insecticides, it has become desirable to prepare completely pure α-naphthyl methyl ketone (I). Thereby, in this paper, we report the preparation of (I) from α-naphthaldehyde (II) and diazomethane according to the Arndt-Eistert reaction. The synthesis of this compound was reported by many authors, but we found no literature on the behavior of diazomethane towards (II). Depending on the Arndt-Eistert reaction, the scheme of synthetic reaction may be expressed as in Fig. 1. This reaction yields in the first step a pyarzole derivative, but this intermediate compound is unstable and decomposes very easily eliminating nitrogen. It may be converted into three condensation products (ketone, ethylene oxide or homologous aldehyde). Therefore, (II) was kept in diazomethane ether solution at room temperature until nitrogen evolution ceased. (I) and ethlyene oxide derivative could be isolated from the mixture of reaction products by treatment with saturated NaHSO3 solution. (I) was separated by distillation, showing b. p.7mm 154°, and it was identified as the semicarbazone of mp. 209°. From the crystalline addition compounds of NaHSO3, the unreacted (II) and a neutral substance were liberated by means of Na2CO3. The neutral crystalline substance thus obtained is colorless prism, melts at 140_??_141° and the deduced empirical formula is C13H12O2.
社団法人日本農芸化学会の論文