Trifluoroacetic acid → (2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methane

Participants

Reaction Conditions

Reaction Steps

(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methanol (15.54 g, 54 mmol) and triethylsilane (7.53 g, 0.064 mol) were dissolved in 150 ml of methylene chloride and the solution cooled to 0° C. and blanketed with nitrogen. A solution of 7.39 g (64.8 mmol) of trifluoroacetic acid in 70 ml of methylene chloride was added with stirring and cooling and the mixture was allowed to react for 2 hours. The reaction mixture was then poured into saturated aqueous sodium bicarbonate, more methylene chloride added, and the organic layer recovered. This was extracted with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain 19.34 g of orange oil. This was purified by preparative liquid chromatography eluting with a 5:95 mixture of acetone and hexane to obtain 3.95 g (27 percent of theory) of the title compound as an oil. The proton nmr spectrum was consistent with the assigned structure.

Provenance & Evidence