Process for manufacturing n-acyl derivatives of...

C - Chemistry – Metallurgy – 07 – C

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260/508.5, 260/5

C07C 233/45 (2006.01) C07C 237/00 (2006.01) C07D 307/77 (2006.01)

Patent

CA 1066304

ABSTRACT OF THE DISCLOSURE Condensation of the addition product of glyoxylic acid and amides with hydroxyaryl compounds is effected by a first step, wherein the reaction is carried out hot, at a temperature below 60°C, of an aliphatic amide having at the most 4 carbon atoms selected from the group of acetamide, chloracetamide, propionamide, acrylamide and butyramide, on an aqueous solution of glyoxylic acid. Then in a second step, after the addition of acetic acid and ga- seous hydrochloric acid, condensation is effected at a tempe- rature below 35°C of the carboxamidoglycolic acid with an excess reaching 500% of hydroxyaryl compound selected from the group comprising phenyl and its alkyl derivatives, their halogen derivatives, polyphenols and their ethers and beta- naphthol. After the condensation of said second step, the volatile products are removed by vacuum sidtillation. When the hydroxyaryl compound is phenol, the crude product result- ing from this distillation is taken up in nitromethane or water, which are a non-solvent of the N-acyl derivative of parahydroxyphenylglycine but a solvent of the corresponding ortho derivative; the proportion of the para derivative in the resulting compound is then of the order of 100%.

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