Water → HCID 14053357, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 33.6 g (0.2 mol) of 3-hydroxy-4-methoxybenzoic acid and 26.8 g (0.4 mol) of potassium hydroxide (85%) in 200 ml of toluene and 200 ml of dimethyl sulfoxide is dewatered at 140° C. in a sulfonating flask equipped with a water separator. The toluene is distilled off and the mixture is then cooled to 90° C. and 43 g (0.2 mol) of 3,4-dichlorobenzotrifluoride, 1.1 g of potassium iodide and 0.2 g of copper filings in 20 ml of dimethyl sulfoxide are added. The mixture is kept for 30 hours at 150° C. and the solvent is then distilled off under a high vacuum. The residue is dissolved in 250 ml of water, the solution is filtered, the filtrate is acidified with 100 ml of 2N HCl in 200 g of ice and the precipitate obtained is filtered with suction, then washed with water and vacuum-dried at 80° C., affording 58 g of 3-(2-chloro-4-trifluoromethylphenoxy)-4-methoxybenzoic acid. Melting point 162°-165° C.

Provenance & Evidence