Sodium Hydroxide → 4-[(4-Chlorophenyl)sulfanyl]-3-nitrobenzoic acid

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Reaction Steps

The above-mentioned ethyl 4-(4-chlorophenylthio)-3-nitrobenzoate (760 mg, 2.25 mmol) was dissolved in a mixture of ethanol (5 mL) and THF (10 mL). After addition of 2M aqueous sodium hydroxide (2.25 mL, 4.50 mmol), the mixture was stirred at room temperature for 4 hours and placed under reduced pressure to distill the solvent off. To the residue were added water (20 mL) and 2M aqueous hydrochloric acid until the mixture reached pH 2. The precipitated crystalline product was collected by filtration, washed successively with water (5 mL×3), a mixture (5 mL) of ethanol and water (1/4) and hexane (5 mL×2), and dried at 40° C. under reduced pressure, to obtain 703 mg (yield 100%) of the titled compound as a yellow crystalline product.

Provenance & Evidence