Issue 17, 2019

Eco-efficient synthesis of 2-quinaldic acids from furfural

Abstract

Quinaldic acids are important fine chemicals. Nowadays, industrial methods to synthesize quinaldic acids rely heavily on a three-step process established based on the Reissert reaction, which involves however the use of highly toxic potassium cyanide. In this paper, a novel cyclization of aniline with ethyl 4,4-diethoxycrotonate was realized, which offered ethyl quinaldate in good yield. Based on this reaction, an eco-efficient method to prepare quinaldic acids was developed, which involves the following three steps: (i) synthesis of ethyl 4,4-diethoxycrotonate through photooxidation of furfural and a consecutive ring-opening alcoholysis; (ii) cyclization of ethyl 4,4-diethoxycrotonate with aniline, and (iii) hydrolysis of the generated ethyl quinaldate. This new method not only avoids the use of toxic potassium cyanide but also meets many salient features of green chemistry, such as the use of bio-based feedstocks, environmentally benign metal-free conditions and good reaction yields.

Graphical abstract: Eco-efficient synthesis of 2-quinaldic acids from furfural

Supplementary files

Article information

Article type
Paper
Submitted
09 تیر 1398
Accepted
02 مرداد 1398
First published
02 مرداد 1398

Green Chem., 2019,21, 4650-4655

Eco-efficient synthesis of 2-quinaldic acids from furfural

M. Li, X. Dong, N. Zhang, F. Jérôme and Y. Gu, Green Chem., 2019, 21, 4650 DOI: 10.1039/C9GC02206F

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