4-Hydroxybenzyl cyanide

104-47-2

14191-95-8

General procedure for the synthesis of 2-(4-hydroxyphenyl)acetonitrile from 2-(4-methoxyphenyl)acetonitrile: 2-(4-methoxyphenyl)acetonitrile (500 g, 3.397 mol) was slowly added to a stirred suspension of aluminum chloride (1358.86 g, 10.19 mol) in toluene (2100 ml) over a period of 20-30 min at room temperature. The reaction mixture was gradually warmed up to 70°C and maintained at this temperature for 4-6 hours. The reaction progress was monitored by TLC (unfolding agent: 5% ethyl acetate/hexane). Upon completion of the reaction, the mixture was slowly poured into pre-cooled aqueous hydrochloric acid solution (3000 ml of water; 667 ml of concentrated hydrochloric acid), keeping the temperature below 20°C. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 500 ml). The organic layers were combined, washed with water (2 x 500 ml) and dried over anhydrous sodium sulfate (50 g). The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was stirred with a mixture of hexane (800 ml) and ethyl acetate (40 ml) for 1 h. The solid product was collected by filtration and washed with hexane (300 ml). The resulting light brown product was dried under vacuum at 35-40°C. Yield: 431.6 g (95.41% yield); HPLC purity: 99.56%; Melting point: 70-71.6 °C (DMSO-d6).1H NMR (DMSO-d6, δ ppm): 9.55 (s, 1H, ArOH), 7.15 (d, 2H, ArH), 6.80 (d, 2H, ArH), 3.84 (s, 2H , CH2).13C NMR (DMSO-d6, δ ppm): 156.99, 129.40, 121.21, 119.80, 115.85, 21.73. IR (KBr, cm-1): 3340.71, 2268.29, 1614.42, 1516.05, 1446.61, 1408.04, 1263.37, 1222.37, 1222.04. 1263.37, 1222.87, 1105.21, 943.19, 819.75, 759.95, 707.88, 578.64. GC-MS (m/z): 133 (base peak), 106, 90, 78.