4-Toluenesulfonyl chloride → 2-Methylcyclopentyl 4-methylbenzene-1-sulfonate

Participants

Reaction Steps

A three-necked flask (500 cc) equipped with a mechanical stirrer was charged with 2-methylcyclopentyl alcohol (21.19, 0.210 mol) and p-toluenesulfonyl chloride (48.3 g, 0.252 mol), followed by the addition of pyridine (170 ml) under ice cooling to form a solution. The solution was stirred for 10 h as it was warmed gradually to room temperature. After completion of the reaction, the reaction mixture was poured into ice water and stirred thoroughly. Following extraction with ether (200 mL×3), the organic layers were washed with 2N HCl, water and saturated brine and dried with anhydrous magnesium sulfate. After the desiccant was removed, the solvent was distilled off under vacuum to give 2-methylcyclopentyl p-toluenesulfonate as a colorless clear oil (49.7 9; yield=92.8%). 1H-NMR(CDCl3,TMS,ppm): δ0.85(3H,d,J=7.5Hz), 1.41-2.10(TH,m), 2.43(3H,s), 4.42 and 4.80(total 1H, each m), 7.33(2H,d,J=9.0Hz), 7.80(2H,d,J=9.0Hz).

Provenance & Evidence