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

Temperature

25 °C

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 adjusted to a pH of 10.5 at 20 to 25° C. using 78.4 g of KOH solution (50% strength by weight aqueous solution, 0.7 mol). Metered into this solution then at a pH of 10.5, over the course of three hours, were 95.4 g (0.5 mol) of decanoyl chloride. The pH was held at 10.5 using 44.0 g of KOH solution (50% strength by weight aqueous solution, 0.392 mol), and the temperature was held at 20 to 25° C. The batch was stirred for one hour thereafter. Subsequently the reaction mixture was adjusted to a pH of 8 at 20 to 25° C. using 10 g of HCl solution (32% strength by weight aqueous solution) and adjusted to a pH of 1.5 to 3 at 65 to 70° C. using 55 g of HCl solution (32% strength by weight aqueous solution). The reaction mixture was cooled to room temperature (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 131.5 g (90.0% 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. customwas adjusted to a pH of 10.5 at 20 to 25° C.
2. customover the course of three hours
3. customwas held at 20 to 25° C
4. customwas adjusted to a pH of 8 at 20 to 25° C.
5. customadjusted to a pH of 1.5 to 3 at 65 to 70° 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-8ba66b74092e42a395b64085e173f634

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901342B2