文献类型：期刊文献

英文题名：Practical and Scalable Synthesis of 1,3-Adamantanediol

作者：Hao, Fuhao[1];Chen, Rener[2];Yang, Zuoguo[1];Chen, Jianhua[2];Bai, Zhongjia[1];Xu, Jing[2];Yu, Zhongbao[2];Maimaiti, Buawa[2];Guo, Wanqin[2];Feng, Hao[2]

机构：[1]East China Univ Sci & Technol, Sch Chem Engn, Shanghai 200237, Peoples R China;[2]RongYao Biotech, Taizhou 318000, Zhejiang, Peoples R China

年份：2024

卷号：28

期号：3

起止页码：738

外文期刊名：ORGANIC PROCESS RESEARCH & DEVELOPMENT

收录：;EI(收录号：20240815582564);WOS:【SCI-EXPANDED(收录号:WOS:001174731500001)】；

语种：英文

外文关键词：acyl chloride; decarbonylation; DFT; triethylamine; thionylchloride

摘要：A new method for the efficient synthesis of 1,3-adamantanediol is proposed. It has the advantages of good reaction selectivity, high isolated yield, easy purification, and safe operation. 3-Hydroxyadamantane-1-carboxylic acid reacts first with thionyl chloride to form 1,3-dichloro adamantane, which is then converted to 1,3-adamantanediol in a "triethylamine-water" solution. Three reaction types are involved: chlorination, decarbonylation, and hydrolysis. Under optimal reaction conditions, total isolated yields of up to 95% and purities of up to 99% were achieved. Isolated yields of 100 g per batch have been achieved, with potential for industrial production. We completed the decarbonylation of acyl chloride without the use of a metal catalyst. In addition, the reaction mechanism was investigated by combining experimental data and density functional theory.