p-Toluenesulfonic acid → Benzene, 1-(diethoxymethyl)-4-fluoro-

Participants

Reaction Steps

A mixture of 4-fluorobenzaldehyde, compound (5) (20 g, 17.3 ml, 161.15 mmol), triethylorthoformate (29.85 g, 33.5 ml, 201.43 mmol) and para-toluenesulphonic acid (0.28 g, 1.61 mmol ) in ethanol (100 ml) was stirred for 16 hours under a nitrogen atmosphere at ambient temperature. The mixture was treated with anhydrous sodium carbonate to pH 9, stirred for a further five minutes and then filtered and the filtrate evaporated to dryness. Purification by flash column chromatography eluting with iso-hexane/dichloromethane (1:1) and then with iso-hexane/ethyl acetate (9:1) gave a clear oil, compound (6)(22.77 g, 71% Yield).

Provenance & Evidence