Chloroace tic acid

The following protocol illustrates the modification of a dextran polymer with chloroace-tic acid. 

Heuma nn II Process. In the Heumann II process, starting from anthranilic acid,, V-phcnylglycine-o-carboxylic acid, prepared from anthranilic acid and chloroace-tic acid, is added in the form of the alkali metal salt 13 to a KOH/NaOH melt at 200 °C to produce indoxylcarboxylic acid salt 14. After hydrolysis and decarboxylation, the product is oxidized in air to yield indigo [19],... 

Mercaptoacetic acid, also known as thioglycolic acid, is prepared from the continuous reaction of chloroace-tic acid with two molar equivalents of aqueous ammonium or metal hydrosulfide. The reaction is nm under autogenous H2S overpressure, derived from the neutralization of the chloroacetic acid with one equivalent... 

These compounds are prepared starting from chloroace-tic acid or its ethyl ester. For chains longer than acetic, cya-noethylation and hydrolysis of the nitrile obtained leads to the propionic chain, alkylation with ethyl 4-bromobutyrate and saponification leads to the butyric chain. The propane-sulfonic chains are particularly accessible by means of ring opening of propane-sultone. 

Kakiuchi H, Tijima T (1980) The ring-opening reactions of propylene oxide with chloroace-tic acids. Tetrahedron 36(8) 1011-1016... 

---