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

Participants

Reaction Conditions

Reaction Steps

165.7 g (1.2 mol) of para-hydroxybenzoic acid were first dissolved in 400 ml of water and 600 ml of isopropanol and this solution was admixed at 10 to 15° C. with 276.1 g of KOH solution (50% strength by weight aqueous solution, 2.46 mol). The resulting pH was 14. Metered into this solution over the course of two hours, then, at 10 to 15° C., were 228.8 g (1.2 mol) of decanoyl chloride, and the batch was stirred for 15 minutes at 10 to 15° C. thereafter. At the end of the after-stirring, the pH of the reaction mixture was 9.5. The reaction mixture was subsequently admixed at 10 to 15° C. with 30 g of HCl solution (32% strength by weight aqueous solution), and the complete solution was heated to 55 to 60° C. and then adjusted to a pH of 1.5 to 3 using 120 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 150 ml of water. The yield after drying under reduced pressure at 100° C. was 314.4 g (89.6% 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