Tetrahydrofuran → 2-(4-Fluorobenzoyl)benzoic acid

Beteiligte Stoffe

Reaktionsschritte

A 1 M solution of lithium aluminum hydride in THF (258 ml, 258 mmol) was added dropwise to a solution of the mixture of 2-(4-fluorobenzyl)benzoic acid and the starting material 2-(4-fluorobenzoyl)benzoic acid, which was isolated in step 1, in THF (200 ml). The reaction mixture was heated to reflux for 2 hours. It was cooled to 0° C. Carefully, methanol (100 ml) and water (50 ml) were added successively. A 10% aqueous solution of sodium hydrogensulphate (500 ml) and a 1 N solution of sodium chloride in water were added. The phases were separated. The aqueous phase was extracted with ethyl acetate (2×300 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (600 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. 5.23 g of [2-(4-fluorobenzyl)phenyl]methanol were isolated by flash chromatography on silica (200 g), using ethyl acetate/heptane 1:1 as eluent.

Herkunft & Nachweise