Benzene → HCID 23369392, compound

Participants

Reaction Steps

To a stirred benzene suspension of NaH (0.39 g, 32.2 mmol) was added a benzene solution of 2-hydroxymethylthiophene (2.0 g, 15.1 mmol). The reaction was stirred 3 h and a benzene solution (10 mL) of chloroacetic acid (1.56 g, 16.6 mmol) was added. The reaction was heated to reflux for 15 h then cooled to room temperature and a small amount of water was cautiously added. The aqueous layer was diluted, separated, acidified and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over MgSO4. Evaporation afforded thien-2-ylmethoxyacetic acid as a tan oil (66%).

Provenance & Evidence