Influence of Carboxylic Acids on the Synthesis of Chlorohydrin Esters from 1,3‐Butanediol

Abstract

The influence of diverse carboxylic acid on the preparation of chlorohydrin esters using a one‐pot esterification–chlorination reaction, in which one of the reagents (chlorotrimethylsilane) acts as solvent, is described. Whereas the acid with low pKa provided higher amounts of the 2‐chloro regioisomer, the ones with higher pKa rendered the 1‐chloro regioisomer in 80% yield. These results are in accordance with the mechanism proposed in a previous article.

Keywords:

• Carboxylic acids
• chlorohydrin esters
• chlorotrimethylsilane
• diol
• halogenation
• regioselectivity

Acknowledgments

The authors are grateful to Secretaría de Estado de Política Científica y Tecnológica of the Spanish Ministerio de Educación y Ciencia (PPQ2003‐02871) and Departament d'Universitats, Recerca i Societat de la Informació (DURSI) (2001SGR00309) for financial support. We thank Montserrat Llovera for GC/MS measurements.