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

Participants

Reaction Conditions

Reaction Steps

798.3 g (5.78 mol) of para-hydroxybenzoic acid were first dissolved in 1980 ml of water and 2970 ml of isopropanol and this solution was admixed at 10 to 15° C. with 1329.7 g of KOH solution (50% strength by weight aqueous solution, 11.84 mol). The resulting pH was 14. Metered into this solution over the course of 100 minutes, then, at 10 to 15° C. were 1106.8 g (5.78 mol) of decanoyl chloride (99.6% strength by weight solution), and the batch was stirred for 15 minutes at 10 to 15° C. thereafter. The reaction mixture was subsequently admixed at 10 to 15° C. with 149.1 g of HCl solution (31% strength by weight aqueous solution), and the complete solution was heated to 65 to 70° C. and then adjusted to a pH of 1.5 to 3 using 596.5 g of HCl solution (31% 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 750 ml of water. The yield after drying under reduced pressure at 100° C. was 1487 g (88% 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