Formaldehyde → HCID 86704561, compound

Participants

Reaction Steps

To a stirred solution of 2-(4-bromo-phenyl)-propionitrile (27 g, 128.5 mmol) in pyridine (225 mL) was added paraformaldehyde (15.7 g, 514.3 mmol) and a 40% Triton-B solution (in methanol) (14.4 mL). Then the reaction mixture stirred at room temperature for 16 h. At this time, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (300 mL). The organic layer was washed with a 2N aqueous hydrochloric acid solution (2×200 mL), water (2×100 mL), sodium bicarbonate (2×50 mL), a saturated aqueous sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. Flash chromatography afforded 2-(4-bromo-phenyl)-3-hydroxy-2-methyl-propionitrile as colorless oil (25.9 g, 84%).

Provenance & Evidence