Hydrochloric Acid → Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of tetrahydo-4-pyranol (5.00 g; 48.9 mmol) in pyridine (30 mL) at 0-5° C. was added portionwise p-toluenesulfonyl chloride (13.9 g; 73.4 mmol). The mixture slowly warmed to room temperature, stirred overnight and poured onto 30 mL conc. HCl in ice. After stirring 15 minutes the solid was filtered and dried in vacuo. Trituration with t-butyl methyl ether provided 11.7 g of the desired product. 1H NMR (CDCl3) δ 7.82 (d, 2H), 7.35 (d, 2H), 4.70 (m, 1H), 3.88 (m, 2H), 3.47 (m, 2H), 2.46 (s, 3H), 1.86 (m, 2H), 1.76 (m, 2H).

Provenance & Evidence