Sodium Chloride → HCID 54401809, compound

Participants

Reaction Steps

Thionyl chloride (40 ml) is slowly added at 0° C. with stirring to a suspension of 2-acetamido-3-hydroxy-4-methoxybenzyl alcohol (2.5 g, 12.0 mmol) and anhydrous CH2Cl2 (30 ml). After the reaction mixture has warmed to RT, it is stirred for 1 h and then stirred at 50° C. for a further 1.5 h. The reaction solution is concentrated in vacuo and then coevaporated with toluene (3 times). The residue obtained is dissolved in a mixture of toluene and DMF (8:1, 45 ml) and added dropwise to a solution of KCN (1.0 g, 15.4 mmol) in 18-crown-6 (4.07 g, 15.4 mmol) and absolute DMF (55 ml). The reaction solution is stirred overnight at RT and then poured into a half-concentrated aqueous NaCl solution, extracted with ethyl acetate (5 times), dried over MgSO4, filtered off and concentrated in vacuo. For further purification, the crude product is filtered through a silica gel column [petroleum ether/ethyl acetate (6:4)]. The title compound is obtained as colorless crystals (1.28 g). TLC, silica gel (glass plates), petroleum ether/ethyl acetate (6:4), Rf=0.32.

Provenance & Evidence