Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. Like other chloroacetic acids and related halocarbons, it is a potentially dangerous alkylating agent.
Chloroacetic acid is synthesized by the chlorination of acetic acid in the presence of red phosphorus, sulfur, or iodine as a catalyst:
- CH3CO2H + Cl2 → ClCH2CO2H + HCl
It also forms by the hydrolysis
using sulfuric acid
as a catalyst.
Illustrative of its usefulness in organic chemistry is the O-alkylation of salicylaldehyde with chloroacetic acid, followed by decarboxylation of the resulting ether, produces benzofuran.