Facile Selective Acetylation of Primary Alcohols Using Ethyl Acetate in Acidic Medium

• Published in: ChemistrySelect (Weinheim) 2023-06, Vol.8 (21), p.n/a
• Main Authors: Ferreira Pereira da Silva, Igor, Cavalcante dos Santos Giló, Larissa, Campos Reis, Analú, Raimundo da Rocha, Jéssica, Oliveira, Adeildo Junior, Fonseca Goulart, Henrique, Barbosa Bernardo, Vanderson, Euzébio Goulart Santana, Antônio
• Format: Article
• Language: English
• Subjects: Acetylation; alcohol; ethyl acetate; TsOH
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202301291

Esters are demanded in a varied range of human industries and, although the classical methods for their production have been known since the late 19th century, the search for improved and sustainable protocols to prepare this class of compounds is yet invaluable. An efficient, fast and straightforward method has been stablished, using TsOH and EtOAc for the acetylation of primary alcohols, with yields ranging from 81 to 98 %, depending on the groups near the hydroxyl group. A slight variation of the protocol might also be applied to secondary alcohols with moderate to high yields (65 to 91 %). Finally, the methodology can be used to selectively acetylate primary and secondary alcohols in the presence of tertiary or phenolic hydroxyl groups. We report a highly efficient and cost‐effective method for the acetylation of primary alcohols with yields ranging from 81 to 98 %. An adaptation of the protocol might also be applied to secondary alcohols with moderate to high yields (65 to 91 %). The methodology is selective towards primary and secondary alcohols in the presence of tertiary or phenolic hydroxyl groups.