Sulfuric Acid → HCID 178526162, compound

Participants

Reaction Conditions

Reaction Steps

4-Phenoxyaniline (30 g, 162 mmol) was added in portions to a stirred solution of 98% w/v sulphuric acid (93 ml) in water (480 ml). The mixture was heated at 80° C. for 30 minutes and then cooled to 0°-5° C. A solution of sodium nitrite (13.5 g, 196 mmol) in water (60 ml) was added dropwise and the mixture was stirred for 45 minutes at 0° C. The excess nitrous acid was destroyed with sulphamic acid. The solution was added to a stirred mixture of 2-mercaptoacetic acid (14.7 ml, 211 mmol), basic copper carbonate (10.8 g, 49 mmol) and acetone (180 ml) at 0° C. The mixture was warmed to ambient temperature. After 1 hour ethyl acetate (200 ml) was added and the insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The combined extracts were then extracted with a saturated solution of sodium hydrogen carbonate. The combined aqueous extracts were acidified to pH 2 by the addition of 2M hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed by evaporation to give 4-phenoxyphenylthioacetic acid as an oil (12.3 g) having a satisfactory NMR spectrum (200 MHz, CDCl3); 3.61 (s,2H), 6.93-7.46 (m,9 aromatic H), after purification by flash chromatography on silica (Merck Kieselgel Art 9385) using ethyl acetate/dichloromethane (1:1 v/v).

Provenance & Evidence