ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A new procedure for the synthesis of 2-[(4-dodecyloxyphenyl)sulfonyl]butanoic acid

Yun-Long Shi, Ling Wang, Chao Qian, Ming Tao, Zu-Tai Liao, and Xin-Zhi Chen

Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, 310027 Hangzhou, China

E-mail: xzchen@zju.edu.cn

Abstract: A new, practical and cost-effective route for scalable synthesis of 2-[(4-dodecyloxyphenyl)sulfonyl] butanoic acid, a key intermediate of a new cyan dye-forming coupler containing a sulfone group, was developed by adopting phenol as the starting material. The synthesis was accomplished in five steps with etherification, chlorosulfonation, reduction, nucleophilic reaction by C-S coupling and hydrolyzation. An important objective of the new synthetic route was the synthesis of 2-[4- (dodecyloxyphenyl)sulfonyl]butanoate. Overall yield obtained at optimized conditions increased to 66 %. The synthetic strategy was proven to be a process enabling rapid delivery of the target product with high purity.

Keywords: cyan dye-forming coupler – 2-[(4-dodecyloxyphenyl)sulfonyl]butanoic acid – phenol – C-S coupling.

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0125

Chemical Papers 69 (9) 1237–1243 (2015)