Citric Acid → HCID 86593874, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1168 mg (6.01 mmol) 5-Hydroxy-benzo[b]thiophene-2-carboxylic acid (Misra, T., et al., Spectrochim. Acta Part A 57 (2001) 2795–2808) in 30 ml dichloromethane were added 1186 mg (15 mmol) pyridine. The mixture was cooled to 0° C. and a solution of 1968 mg (14 mmol) benzoyl chloride in 15 ml dichloromethane was added within 0.5 h. The reaction mixture was warmed to room temperature and added to 5% aqueous citric acid. The aqueous phase was extracted twice with dichloromethane, the solvent of the organic phases was removed and the residue was chromatographed on silica gel (dichloromethane/methanol 19:1 and then dichloromethane/methanol 19:1 with 2% acetic acid) to yield 1180 mg (3.96 mmol) O-Benzoyl-5-hydroxybenzothiophene-2-carboxylic acid (2) as colorless crystals, mp. 235–236° C.

Provenance & Evidence