Sodium Bicarbonate → (6-Chloropyridin-2-yl)methanol

Participants

Reaction Steps

A solution of 2-acetoxymethyl-6-chloropyridine (17.3 g; 93.3 mmol), prepared as in step 2, in 250 mL 10% aqueous HCl was heated at reflux for 1.5 hours. The reaction mixture was cooled to room temperature and poured into 300 mL saturated aqueous sodium bicarbonate. The solution was adjusted to pH 9 by the addition of solid sodium bicarbonate. The solution was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated. The 6-chloro-2-hydroxymethylpyridine was used with no further purification.

Provenance & Evidence