Acylation of 2-methoxynaphthalene with acetic anhydride over silica-embedded triflate catalysts

Abstract

Silica sol–gel immobilized triflate compounds like La(OTf) 3, tert-butyldimethylsilyl trifluoromethanesulfonate (BDMST) and triflic acid (HOTf) were tested in the acylation of 2-methoxynaphthalene with acetic anhydride, leading to 1-acetyl-2-methoxynaphthalene as the major product. The reaction only proceeded with good yields on BDMST and HOTf catalysts, while La(OTf) 3 presented a low activity. For BDMST in solvent-free conditions, the resulting TOF was superior to that reported in literature for other heterogeneous catalysts and even for homogeneous triflates. The rates of reactions in various solvents strongly depend on the donor number of these solvents.