4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

Participants

Reaction Conditions

Reaction Steps

105 mg of p-toluenesulfonyl chloride is added to a solution of 156 mg of 2-(RS)-(2-hydroxyethyl)-2,3-dihydro-5-benzyloxy-4,6,7 -trimethylbenzofurane in 0.5 ml cooled to 0° C. The reaction mixture is stirred for 3 hours, then it is acidified and extracted. The organic extracts are dried and evaporated, thus giving 185 mg of raw product, which is then purified with chromatography (SiO2). 153 mg of p-toluenesulfonate of 2[2,3-dihydro-5-benzyloxy-4,6,7-trimethyl-2-(RS)benzofuranyl]ethyl are obtained. IR (KBr): 1359, 1177 cm-1 (νSO2). The product thus obtained is then solubilized in 2 ml of anhydrous tetrahydrofurane and added to a suspension of 45 mg of lithium and aluminum hydride in 5 ml of anhydrous tetrahydrofurane. The reaction mixture is stirred in an inert atmosphere for 30 minutes. The reaction process is carried out using the same procedure described in example 1. 82 mg of a white solid are obtained. m.p. 65°-67° C. IR (KBr): 1595 (νC--C), 1237 cm-1 (νC--O--C); 1H-NMR (CDCl3): δ 7.5-7.1 (5H,m), 4.8-4.4 (1H,m), 4.7 (2H,s), 3.3-2.5 (2H,m), 2.2 (6H,s), 2.1 (3H,s), 1.9-1.5 (2H,m), 1.0-(3H,t).

Provenance & Evidence