4-Toluenesulfonyl chloride → 3-Methylcyclopentyl 4-methylbenzene-1-sulfonate

Participants

Reaction Steps

A round-bottomed flask (100 cc) was charged with 3-methylcyclopentyl alcohol (5.0 g, 49.9 mmol) and p-toluenesulfonyl chloride (10.0 g, 52.5 mmol), followed by the addition of pyridine (50 mL) under ice cooling to form a solution. The solution was stirred for 8 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. After extraction with ether (100 mL×2), 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 3-methylcyclopentyl p-toluenesulfonate as a colorless clear oil (11.7 g; yield=92.5%). MP: <30° C. 1H-NMR(CDCl3,TMS,ppm): δ0.93 and 1.00(total 3H, each d,J=6.0Hz), 1.20-2.30(7H,m), 2.48(3H,s), 4.97(1H,m), 7.38(2H,d,J=8.0Hz), 7.85(2H,d,J=8.0Hz).

Provenance & Evidence