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A Facile Preparation of Hydroxycinnamyl Alcohols withSimultaneous Protection of Phenol Groups as Carbonate
Author(s) -
Panzella Lucia,
DellaGreca Marina,
Longobardo Luigi
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802099
Subject(s) - sodium borohydride , chemistry , phenol , chloroformate , organic chemistry , alkyl , phenols , alcohol , methanol , aqueous solution , catalysis
A novel procedure for reduction and simultaneous protection of phenol groups of hydroxycinnamic acids to the related alcohols has been developed. During the formation of mixed anhydrides from the acids and an alkyl chloroformate, the phenol was protected as carbonate, and the mixed anhydrides were reduced with an aqueous solution of sodium borohydride. Free phenols were obtained by deprotection under mild conditions with 30% aq. NH 4 OH in methanol. O ‐protected phenolic alcohols can be converted by standard methods into orthogonal protected derivatives. This rapid and efficient synthetic method offers a simple and high‐yield preparation of these important fine chemicals, overcoming the tedious and costly procedures associate with the use of strong reducing agents such as LiAlH 4 and DIBAL−H.