Tetrahydropyranyl ethers were synthesized from corresponding alcohols or phenols and 3,4-dihydro-2H-pyran using acetic acid assisted copper o-toluenesulfonate as a synergistic catalyst at room temperature under a solvent-free condition. The catalytic activity of acetic acid assisted copper o-toluenesulfonate was much higher than that without acetic acid under the same conditions. Only the molar ratio 0.3 mol% of copper o-toluenesulfonate to alcohol or phenol was efficient to complete the reaction in a short time. After reaction, the copper o-toluenesulfonate could be recovered easily by simple phase separa-tion and reused many times without distinct loss of its catalytic activity. The structures of products were characterized by IR, 1H NMR spectra and elemental analysis.

Key words: tetrahydropyranylation, copper o-toluenesulfonate, alcohol, phenol, acetic acid