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

HRID 1401747Notes

Reaction equation

HRID 1401747 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].[C:13](Cl)(=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O.C(O)(C)C>[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric Acid2×HCID 14797Potassium HydroxideHCID 66982Decanoyl chloride

Product 1

HCID 3608562Benzoic acid, 4-((1-oxodecyl)oxy)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
12.5 °C

Procedure

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.

Workup

  1. customover the course of 100 minutes
  2. customat 10 to 15° C.
  3. temperaturethe complete solution was heated to 65 to 70° C.
  4. temperatureThe reaction mixture was cooled to 20 to 25° C.
  5. filtrationthe solid was filtered off on a suction
  6. filtrationfilter
  7. washwashed ten times with 750 ml of water
  8. customThe yield
  9. customafter drying under reduced pressure at 100° C.

Sources & evidence

ORD record
ord-5846fae88f1a4d8bb23af9620b84d826
Source dataset
uspto-grants-2014_12
Patent number
US08907118B2

Reaction notes

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