1. Practical and Scalable Synthesis of 1,3-Adamantanediol
- Author
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Hao, Fuhao, Chen, Rener, Yang, Zuoguo, Chen, Jianhua, Bai, Zhongjia, Xu, Jing, Yu, Zhongbao, Maimaiti, Buawa, Guo, Wanqin, and Feng, Hao
- Abstract
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.
- Published
- 2024
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