3-Pyridinemethanol → HCID 12713103, compound

Participants

Reaction Conditions

Reaction Steps

10.5 g. of 3-hydroxymethyl-pyridine are dissolved in 60 ml. of anhydrous benzene. The solution is stirred at 20° C. and 7.6 g. of 4-fluorobenzoic acid chloride dissolved in 60 ml. of benzene are added dropwise thereto. The reaction mixture is refluxed for 30 minutes and then cooled to 20° C. The precipitated 3-hydroxymethyl-pyridine hydrochloride is filtered off. The filtrate is extracted with 250 ml. of 5% aqueous hydrochloric acid. The separated aqueous acidic layer is washed with 50 ml. of diethyl ether and then adjusted to pH=9 with 20% aqueous sodium carbonate solution. The basified solution is extracted three times with 50 ml. each of diethyl ether, the combined ether extracts are dried with anhydrous sodium sulfate, filtered and the filtrate is evaporated. The evaporation residue is dissolved in 80 ml. of a 1:1 mixture of isopropanol and ether and etheric hydrogen chloride solution is added to adjust the pH-value to 2. The precipitated acid addition salt is separated by filtration and recrystallized from a mixture of equal values of acetone and ethanol. 8.5 g. of 3-[ (4-fluorobenzoyl)-oxymethyl]-pyridine (67.7% of theoretical yield) are obtained; m.p.: 142°-143° C.

Provenance & Evidence