2-Chloroethanol → HCID 52527969, compound

Participants

Reaction Conditions

Reaction Steps

17.5 g (0.106 mol) of 4-dimethylamino benzoic acid was dissolved in 80 mL of dimethyl acetamide and added drop wise over 30 minutes to a suspension of 5.32 g (0.133 mol) of sodium hydride (60% in mineral oil) in 50 mL dimethyl acetamide. It became difficult to stir the suspension and an additional 30 mL of dimethyl acetamide was added. 7.2 mL (8.64 g, 0.107 mol) of 2-chloro-ethanol was added and the reaction mixture was heated to 105° C. The reaction was allowed to continue 16 hours at 105° C. The mixture was allowed to cool down to room temperature and the formed sodium chloride was removed by filtration. The solvent was removed under reduced pressure and the residue was crystallized from 400 mL of methanol/water 1/7. The crude 2-hydroxyethyl-(4-dimethylamino benzoate) was isolated by filtration and recrystallized from 200 mL of methanol/water 1/3. 15 g of 2-hydroxyethyl-(4-dimethylamino benzoate) was isolated (m.p. 88-90°).

Provenance & Evidence