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Synthesis of DL ‐2‐( p ‐hydroxyphenyl)glycine by the ammonolysis of p ‐hydroxymandelic acid obtained by the condensation of phenol with glyoxylic acid
Author(s) -
Powar Netaji P.,
Chandalia Sampatraj B.
Publication year - 1989
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.280460306
Subject(s) - mandelic acid , glyoxylic acid , chemistry , glycine , phenol , ammonia , condensation , salt (chemistry) , yield (engineering) , condensation reaction , ammonium chloride , nuclear chemistry , organic chemistry , catalysis , amino acid , biochemistry , physics , materials science , metallurgy , thermodynamics
Synthesis of DL ‐2‐( p ‐hydroxyphenyl)glycine by the ammonolysis of p ‐hydroxymandelic acid obtained by the condensation of phenol and glyoxylic acid was investigated. Different procedures for the isolation of p ‐hydroxymandelic acid from the product mixture after the condensation step were considered. The ammonolysis of the mandelic acid could be suitably carried out at 115°C using a 10:1 mole ratio of ammonia to p ‐hydroxymandelic acid in the presence of ammonium chloride. A yield of glycine as high as 92% could be obtained when an overall conversion of the mandelic acid was about 80 %. The reaction was found to be first order with respect to the mandelic acid up to a reaction period of 6 h.