Hydrochloric Acid → (3,5-Dichloropyridin-4-yl)methanol

Temperature

0 °C

A cold (0° C.) solution of 4-formyl-3,5-dichloro-pyridine (3.0 g) in ethanol (50 mL) is treated with sodium borohydride (0.7 g), portionwise, during 5 minutes. The resulting mixture is stirred at 0° C. for 10 minutes, and then treated with aqueous hydrochloric acid (5 mL; 2 M), followed by basification to pH 7 by treatment with saturated aqueous sodium hydrogen carbonate solution. The mixture is diluted with water (500 mL) and extracted with ethyl acetate (4×150 mL). The combined organic washings are dried over magnesium sulfate, and the solvent removed under reduced pressure. The resulting residue is recrystallised from t-butyl methyl ether to give 4-hydroxymethyl-3,5-dichloropyridine (2.0 g), in the form of a white solid, m.p. 87-88° C.

1. extractionextracted with ethyl acetate (4×150 mL)
2. dry with materialThe combined organic washings are dried over magnesium sulfate
3. customthe solvent removed under reduced pressure
4. customThe resulting residue is recrystallised from t-butyl methyl ether

ORD record

ord-6bc543b7552b46418ba4461c00bbc2f1

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06096768