122-94-1Relevant articles and documents
Synthesis of 4-[(1R,4R)-3-oxo-p-menthan-2-ylidenemethyl]benzoic acid and its esters
Drushlyak,Kutulya,Pivnenko,Vashchenko
, p. 622 - 627 (2005)
Carbonylation of (E)-2-(4-halobenzylidene)-p-menthan-3-ones, catalyzed by PdCl2(PPh3)2, gave a distereometric mixure of 4-[(1R,4R)- and (1R,4S)-3-oxo-p-menthan-2-ylidenemethyl]benzoic acids, whose reaction with phenols gave 1R,4R diastereomers of the corresponding esters. 2005 Pleiades Publishing, Inc.
Para -Selective hydroxylation of alkyl aryl ethers
Zhu, Runqing,Sun, Qianqian,Li, Jing,Li, Luohao,Gao, Qinghe,Wang, Yakun,Fang, Lizhen
supporting information, p. 13190 - 13193 (2021/12/16)
para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(ii) catalyst, hypervalent iodine(iii) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.
Scalable and Phosphine-Free Conversion of Alcohols to Carbon-Heteroatom Bonds through the Blue Light-Promoted Iodination Reaction
Liu, Bin,Elder, W. Zachary,Miyake, Garret M.
supporting information, p. 3717 - 3727 (2020/03/04)
One of the fundamental and highly valuable transformations in organic chemistry is the nucleophilic substitution of alcohols. Traditionally, these reactions require strategies that employ stoichiometric hazardous reagents and are associated with difficulty in purification of the by-products. To overcome these challenges, here, we report a simple route toward the diverse conversion of alcohols via an SN2 pathway, in which blue light-promoted iodination is used to form alkyl iodide intermediates from simple unreactive alcohols. The scope of the process tolerates a range of nucleophiles to construct C-N, C-O, C-S, and C-C bonds. Furthermore, we also demonstrate that this method can be used for the preparation and late-stage functionalization of pharmaceuticals, as highlighted by the syntheses of thiocarlide, butoxycaine, and pramoxine.
