4-Hydroxybenzoic Acid → HCID 21315467, compound

Participants

Reaction Steps

To a 1 l three-neck flask were added 70 g of sodium salt of p-hydroxybenzoic acid ##STR4## and 200 ml of N,N-dimethylformamide, and the contents were heated under reflux. To the heated contents, 50 g of β-n-butoxyethyl bromide was dropped over a period of 30 minutes and heating was continued under reflux for further 8 hours. After cooling with water, 300 ml of water and 200 ml of toluene were added to the contents and after shaking, the resulting organic layer was separated, washed with 4 N hydrochloric acid and then with a 20% aqueous solution of sodium hydroxide. After distilling off toluene and heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours, the resulting material was neutralized with hydrochloric acid to precipitate the objective material. After washing with water, the objective material was recrystallized from ethanol to obtain 55 g of p-(β-n-butoxy)ethoxybenzoic acid. The melting point of this material was 114.5°-115° C. and the values of the elemental analysis thereof showed a good agreement with the calculated values as seen below.

Provenance & Evidence