イソシトロネロールの合成 (第2報)

抄録

As a result of examination of the synthetic reaction to obtain isocitronellol (4, 7-dimethyl-3-octan-1-ol) from levulic acid, it was found that the object can be achieved by the following two routes. One is the reduction of the lactone (4, 7-dimethyl-1, 4-octanolide) to glycol with subsequent dehydration, while the other is the ring cleavage of the lactone with hydrogen chloride and ethanol, followed by dehydrochlorination to unsaturated ester, and finally by the Bouveault-Blanc reduction, the respective yield being 14% and 16.5% of the theoretical amount. The formation of isocitronellol from glycol by the first method is accompanied by the formation of 2-methyl-2-isoamyltetrahydrofuran, which is present in the perfume and greatly detracts its aroma, that this method was found to be highly undesirable.