4-Hydroxybenzoic Acid → Benzoic acid, 4-((1-oxodecyl)oxy)-

Participants

Reaction Conditions

Reaction Steps

69.1 g (0.5 mol) of para-hydroxybenzoic acid were first dissolved in 200 ml of water and 300 ml of isopropanol and this solution was admixed at 10 to 15° C. with 127.5 g of NaOH solution (32% strength by weight aqueous solution, 1.02 mol). The resulting pH was 13.7. Metered into this solution over the course of three hours, then, at 10 to 55° C., were 95.4 g (0.5 mol) of decanoyl chloride, and the batch was stirred for 30 minutes at 10 to 15° C. thereafter. The complete solution was subsequently heated to 55 to 60° C. and then adjusted to a pH of 1.5 to 3 using 60.0 g of HCl solution (32% strength by weight aqueous solution). The reaction mixture was cooled to 20 to 25° C. and the solid was filtered off on a suction filter and washed ten times with 75 ml of water. The yield after drying under reduced pressure at 100° C. was 124.8 g (85.4% of theory). According to HPLC and NMR measurement, the product was free from decanoic acid and from unreacted para-hydroxybenzoic acid. The purity of the product is >99.9% by weight.

Provenance & Evidence