Chloroacetic Acid → HCID 178526172, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of thiourea (30.4 g, 0.399 mol) in water (200 mL) was added bromodiphenylmethane (98.8 g, 0.399 mol) at 42 degrees C. The mixture was heated gradually to reflux for 10 minutes. The reaction mixture was then cooled to 50 degrees C. and 5 N NaOH (200 mL) was subsequently added. The reaction mixture was then heated to reflux (101-102° C.) for 30 minutes and subsequently cooled to 60 degrees C. To this reaction mixture was slowly added a solution of chloroacetic acid (53.4 g, 0.565 mol) and NaOH (22.2 g) in water (150 mL) over 45 minutes. The reaction mixture was stirred for another 30 minutes. The reaction was then cooled to room temperature and washed with t-butylmethylether (200 ml) to remove any non carboxylic acid impurities. The aqueous layer was acidified (pH 2.0) using concentrated HCl (50 mL). The resulting precipitate was filtered, washed with water (2×200 mL) and heptane (200 mL) and allowed to air dry to give benzhydrylthioacetic acid (116.8 g, 100%) as a colorless solid. (See U.S. Pat. No. 4,066,686)

Provenance & Evidence