Formaldehyde → 2-Hydroxymethyl-2-phenylheptanenitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1.34 g of 60% NaH in 50 mL of DMF cooled to 0° C. are added 5.14 g (27.4 mmol) of 2-phenylheptanenitrile. After stirring for 30 minutes, 7.6 g (220 mmol) of paraformaldehyde are added portionwise. The reaction medium is stirred at room temperature for 6 hours and then hydrolysed with ice and extracted with diethyl ether. The organic phase is washed with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, filtered and evaporated under pressure. The crude product obtained is chromatographed on silica gel (eluent: 8/2 heptane/ethyl acetate). 4.24 g in the form of a pale yellow oil are obtained in a yield of 71%.

Provenance & Evidence