p-Toluenesulfonic acid → 2-(6-Chlorohexyloxy)tetrahydro-2H-pyran

Participants

Reaction Conditions

Reaction Steps

6-Chlorohexanol (6.85 g, 10 mmol) and p-toluenesulphonic acid (500 mg), were dissolved in dry ether (75 ml) and cooled to 0-5° C. in an ice bath. Dihydropyran (4.3 g, 10 mmol) in dry ether (25 ml) was added dropwise with constant stirring over a 30 minute period. After complete addition, the cooling bath was removed and stirring continued for 16 hours. The solution was extracted with water (50 ml×2), dried (MgSO4), filtered and the solvent evaporated under reduced pressure to leave a pale yellow oil. This oil was shown by 13C NMR spectroscopy to be sufficiently pure to be used without purification in the subsequent reactions. Yield 10.1 g (91%).

Provenance & Evidence