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

Temperature

12.5 °C

138.1 g (1.0 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 235.7 g of KOH solution (50% strength by weight aqueous solution, 2.1 mol). The resulting pH was 14. Metered into this solution over the course of three hours, then, at 10 to 15° C., were 190.7 g (1.0 mol) of decanoyl chloride, and the batch was stirred for 30 minutes at 10 to 15° C. thereafter. At the end of the after-stirring, the pH of the reaction mixture was 8.7. The reaction mixture was subsequently adjusted to a pH of 8 at 10 to 15° C. using 10.4 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 115 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 257.0 g (87.9% 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.

1. customover the course of three hours
2. customat 10 to 15° C.
3. customwas subsequently adjusted to a pH of 8 at 10 to 15° C.
4. temperaturethe complete solution was heated to 55 to 60° C.
5. temperatureThe reaction mixture was cooled to 20 to 25° C.
6. filtrationthe solid was filtered off on a suction
7. filtrationfilter
8. washwashed ten times with 150 ml of water
9. customThe yield
10. customafter drying under reduced pressure at 100° C.

ORD record

ord-2a5af2b546e04325956538b62cd207db

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907118B2