3-Methoxyphenol → 7-Methoxy-1,2,3,4,4a,9b-hexahydro-dibenzofuran

Participants

Reaction Conditions

Reaction Steps

A solution of AuCl3 (0.303 g, 1.0 mmol) and AgOTf (0.770 g, 3.0 mmol) was stirred in anhydrous CH2Cl2 (150 mL) for 2 hours. 3-methoxy-phenol (2.48 g, 20 mmol) in CH2Cl2 (25 mL) was added, followed by addition of cyclohexadiene in CH2Cl2 (25 mL) at 40° C. over two hours. The reaction mixture was stirred at 40° C. overnight. The reaction mixture was passed through a silica gel plug. The filtrate was concentrated. The residue was purified by silica gel chromatography (5-30% CH2Cl2/heptane) to give 0.393 g of the title compound and 0.67 g of 7-methoxy-1,2,3,4-tetrahydro-dibenzofuran.

Provenance & Evidence