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 orthoposition...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 orthoposition 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.In addition to the above aldehydes,ketones and benzyl alcohols,certain 4acyloxybenzyl esters(probably also the 2substituted analogues)such as 4benzoyloxybenzyl benzoate was also found to be reduced to methylphenol by this unusual reduction.展开更多
文摘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 orthoposition 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.In addition to the above aldehydes,ketones and benzyl alcohols,certain 4acyloxybenzyl esters(probably also the 2substituted analogues)such as 4benzoyloxybenzyl benzoate was also found to be reduced to methylphenol by this unusual reduction.
