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Practical and Scalable Synthesis of 1,3-Adamantanediol
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2024-02-08 , DOI: 10.1021/acs.oprd.3c00427 Fuhao Hao 1 , Rener Chen 2 , Zuoguo Yang 1 , Jianhua Chen 2 , Zhongjia Bai 1 , Jing Xu 2 , Zhongbao Yu 2 , Buawa Maimaiti 2 , Wanqin Guo 2 , Hao Feng 2
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2024-02-08 , DOI: 10.1021/acs.oprd.3c00427 Fuhao Hao 1 , Rener Chen 2 , Zuoguo Yang 1 , Jianhua Chen 2 , Zhongjia Bai 1 , Jing Xu 2 , Zhongbao Yu 2 , Buawa Maimaiti 2 , Wanqin Guo 2 , Hao Feng 2
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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.
中文翻译：
1,3-金刚烷二醇的实用且可规模化合成
提出了一种高效合成1,3-金刚烷二醇的新方法。具有反应选择性好、分离收率高、易于纯化、操作安全等优点。3-羟基金刚烷-1-羧酸首先与亚硫酰氯反应形成1,3-二氯金刚烷，然后在“三乙胺-水”溶液中转化为1,3-金刚烷二醇。涉及三种反应类型：氯化、脱羰和水解。在最佳反应条件下，总分离收率高达95%，纯度高达99%。分离产量已达到每批100克，具有工业化生产的潜力。我们在不使用金属催化剂的情况下完成了酰氯的脱羰基反应。此外，结合实验数据和密度泛函理论研究了反应机理。
更新日期：2024-02-08
中文翻译：
1,3-金刚烷二醇的实用且可规模化合成
提出了一种高效合成1,3-金刚烷二醇的新方法。具有反应选择性好、分离收率高、易于纯化、操作安全等优点。3-羟基金刚烷-1-羧酸首先与亚硫酰氯反应形成1,3-二氯金刚烷，然后在“三乙胺-水”溶液中转化为1,3-金刚烷二醇。涉及三种反应类型：氯化、脱羰和水解。在最佳反应条件下，总分离收率高达95%，纯度高达99%。分离产量已达到每批100克，具有工业化生产的潜力。我们在不使用金属催化剂的情况下完成了酰氯的脱羰基反应。此外，结合实验数据和密度泛函理论研究了反应机理。
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