Chloroacetic Acid - Reactivity and Uses

Reactivity and Uses

Illustrative of its usefulness in organic chemistry is the O-alkylation of salicylaldehyde with chloroacetic acid, followed by decarboxylation of the resulting ether, producing benzofuran.

In industry, chloroacetic acid is used in the production of a wide variety of useful compounds; e.g., drugs, dyes, pesticides. Most reactions taking advantage of the high reactivity of the C–Cl bond. It is the precursor to the herbicide glyphosate. The herbicides MCPA (2-methyl-4-chlorophenoxyacetic acid) and dimethoate are prepared by alkylation with chloroacetic acid. Chloroacetic acid is converted to chloroacetyl chloride, a precursor to adrenaline (epinephrine). Displacement of chloride by sulfide gives thioglycolic acid, which is used as a stabilizer in PVC and a component in some cosmetics.

In its largest-scale application, chloroacetic acid is used to prepare the thickening agent carboxymethyl cellulose and carboxymethyl starch.