Methylparaben → para-(pent-4-enoxy)benzoic Acid

Participants

Reaction Steps

2 g of sodium hydroxide, 15 ml of distilled water, 7.6 g of methyl 4-hydroxybenzoate, 0.16 g of tetrabutylammonium bromide and 5.92 ml of 5-bromopent-1-ene are successively placed in a reactor. Vigorous stirring is maintained at ambient temperature for 12 hours. After having added 30 ml of a 2.5M sodium hydroxide solution, the reaction medium is heated at 60–80° C. for 90 minutes. It is subsequently diluted with 120 ml of distilled water and extracted with two times 50 ml of diethylether. The aqueous phase is acidified with 10 ml of concentrated hydrochloric acid in order to make possible the precipitation of the acid. After filtration, washing with distilled water and then drying in a desiccator over P2O5, the acid is obtained with a yield of 93%.

Provenance & Evidence