Water → Methyl 4-(3-chloropropoxy)benzoate

Participants

Reaction Conditions

Reaction Steps

p-Methyl hydroxybenzoate (40 g) and potassium carbonate (54.5 g) in N,N-dimethylformaldehyde (200 ml) were heated with stirring at 100° C. for 1 hour, cooled to 40° C., and then, after adding 1-bromo-3-chloropropane (28.5 ml), the mixture was reacted at 60° C. for 2 hours. After cooling the reaction mixture, water and ethyl acetate were added thereto, and the mixture was separated into layers. The organic layer was washed with water 3 times, concentrated under reduced pressure. To the oily product thus obtained, a small amount of ethyl acetate and n-hexane were added. After the mixture was allowed to stand, the precipitated crystal was collected by filtration and the filtrate was again concentrated under reduced pressure to give the crystal of methy 4-(3-chloropropoxy)benzoate (56.92 g). mp. 52°-55° C.

Provenance & Evidence