Reduction,of aromatic aldehydes and ketones with acyloxy substituent at the ortho-position by NaBH4 in the presence of waters

An unusual reduction of some aromatic aldehydes and ketones by sodium borohydride was discovered. In a THF/H2O or DMSO/H2O solvent system the aromatic aldehydes and ketones with acyloxy substituent on the ortho-position to the carbonyl group can be reduced to the corresponding alkyl phenols. This unusual reduction is: applicable also to the corresponding alcohols of all the above aldehydes and ketones. A putative mechanism was suggested. Tn addition to the above aldehydes, ketones and benzyl alcohols, certain 4-acyloxybenzyl esters(probably also the 2-substituted analogues) such as 4-benzoyloxybenzyl benzoate was, also found to be reduced to methylphenol by this unusual reduction.Chemistry, MultidisciplinarySCI(E)EI中国科学引文数据库(CSCD)1ARTICLE2182-1871