Acryloyl chloride → N-(11-hydroxy-undecyl)-N-methyl acrylamide

Participants

Reaction Conditions

Reaction Steps

11-methylamino undecan-1-ol (10.07 g, 50.0 mmol) was dissolved in dichloromethane (30 ml). A solution of sodium hydroxide (2.40 g, 60.0 mmol) in water (30 ml) was added. The mixture was cooled to −5° C. and a solution of acrylic acid chloride (4.75 g, 52.5 mmol) and BHT (10 mg) in dichloromethane (30 ml) was added dropwise. Once the addition had ended the reaction mixture was stirred for 2 h at −5° C. and for a further 16 h at RT. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with dichloromethane (2×50 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was purified by means of column chromatography (SiO2/ethyl acetate). 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained.

Provenance & Evidence