HO-SAS catalyzed protection and deprotection of aldehydes and alcohols in continuous flow reactors

Abstract

We investigated the flow acetalization of aldehydes and THP protection of alcohols using sulfonic acid-functionalized silica gel having hydroxy moiety (HO-SAS) as the solid acid catalyst. The reaction both aliphatic and aromatic aldehydes reacted with methanol within 5 min of residence time to give acetalization product in good to excellent yield. THP protection of primary, secondary, and tertiary alcohols proceeded well to the corresponding products. Both reactions did not require a neutralization process. Scalable syntheses were also achieved with continuous operation. The deprotection reactions were also effective using HO-SAS packed flow reactors.