3-羟基-1-金刚烷甲基酮的合成及其工艺优化

Synthesis and Process Optimization of 3-Hydroxy-1-acetyladamantane

以1-金刚烷甲酸为起始原料,经混酸（H2SO4/HNO3）氧化得到3-羟基-1-金刚烷甲酸,经酰化、取代、脱羧得3-羟基-1-金刚烷甲基酮。考察了催化剂种类与用量、反应温度、反应时间、乙酰氯与3-羟基-1-金刚烷甲酸物质的量之比对3-羟基-1-金刚烷甲基酮收率的影响,确定了较佳的反应条件为：以吡啶为催化剂,n（吡啶）∶n（3-羟基-1-金刚烷甲酸）=1.5∶1,n（乙酰氯）∶n（3-羟基-1-金刚烷甲酸）=3.5∶1,反应温度为35℃,反应时间为3 h,在该条件下反应总收率约为70%（以1-金刚烷甲酸为基准）。

Treatment 1-adamantanecarboxylic acid with a mixture of sulfuric acid and nitric acid afforded 3-hydroxy-l-adamantaneearboxylie acid. The targeted compound, 3-hydroxy-1- acetyladamantane, was obtained via acylation, substitution and decarboxylation. The amount of catalyst, the type of catalyst, the reaction temperature, the reaction time and the mole ratio between aeetyl chloride and 3-hydroxy-l-adamantanecarboxylic acid were varied step by step to investigate their influence on the yield of 3-hydroxy-l-acetyladamantane. The optimal reaction conditions were obtained as follows： pyridine was selected as catalyst, the molar ratio of pyridine to 3-hydroxy-1- adamantanecarboxylic acid was 1.5：1, the molar ratio of acetyl chloride to 3-hydroxy-1- adamantaneearboxylic acid was 3.5：1 ,the reaction temperature was 35 ℃ and the reaction time was 3 hours. Under these conditions, the overall yield of 3-hydroxy-l-acetyladamantane reached about 70% （based on 1-adamantaneearboxylie acid）.