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Furan derivatives. IC. Role of acetic anhydride in nitration of 3-(2-furyl)acrylic acid

J. Kováč and F. Považanec

Department of Organic Chemistry, Slovak Technical University, 880 37 Bratislava

 

Abstract:  An exothermic reaction, leading to 3-(2-furyl)acrylic anhydride and a little amount of furfurylideneacetone is taking place when reacting 3-(2-furyl)acrylic acid in acetic anhydride above 120°C. The 3-(5-acetyl-2-furyl)acrylic acid was formed under the afore-mentioned conditions only in the presence of H3P04 . The 3-(2-furyl)acrylic anhydride is more stable towards HNO, at temperatures under — 5°C than the free acid and therefore, it was possible to nitrate it in acetic anhydride to 3-(5-nitro-2-furyl)acrylic acid with an HN03—CH3COOH mixture, which means a simplification of the nitration process.

Full paper in Portable Document Format: 322a267.pdf

 

Chemical Papers 32 (2) 267–275 (1978)

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