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

HRID 1401739Notes

Reaction equation

HRID 1401739 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-].[Na+].[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 AcidHCID 14798Sodium 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

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 admixed at 10 to 15° C. with 127.5 g of NaOH solution (32% strength by weight aqueous solution, 1.02 mol). The resulting pH was 13.7. Metered into this solution over the course of three hours, then, at 10 to 55° C., were 95.4 g (0.5 mol) of decanoyl chloride, and the batch was stirred for 30 minutes at 10 to 15° C. thereafter. The complete solution was subsequently heated to 55 to 60° C. and then adjusted to a pH of 1.5 to 3 using 60.0 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 75 ml of water. The yield after drying under reduced pressure at 100° C. was 124.8 g (85.4% 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 three hours
  2. customat 10 to 55° C.
  3. temperatureThe complete solution was subsequently heated to 55 to 60° 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 75 ml of water
  8. customThe yield
  9. customafter drying under reduced pressure at 100° C.

Sources & evidence

ORD record
ord-90bc53574be943b28b7113d7c83df141
Source dataset
uspto-grants-2014_12
Patent number
US08907118B2

Reaction notes

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