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

HRID 1398097Notes

Reaction equation

HRID 1398097 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1>[C:1]([O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 66982Decanoyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
125 °C

Procedure

116.3 g (0.61 mol) of decanoyl chloride were heated in 300 ml of xylene to 125° C. and over the course of 6 hours 69.1 g (0.5 mol) of 4-hydroxybenzoic acid were introduced in portions. The batch was stirred at 125° C. for 1 hour thereafter, cooled to room temperature, and filtered with suction, and the filter product was washed three times with 45 ml of xylene. The yield after drying under reduced pressure at 100° C. was 108.4 g (74% of theory). According to HPLC and NMR measurement, the product was free from decanoic acid and from unreacted para-hydroxybenzoic acid, but contained 0.4% by weight of byproducts such as dimers and trimers of the para-hydroxybenzoic acid.

Workup

  1. additionwere introduced in portions
  2. temperaturecooled to room temperature
  3. filtrationfiltered with suction
  4. washthe filter product was washed three times with 45 ml of xylene
  5. customThe yield
  6. customafter drying under reduced pressure at 100° C.

Sources & evidence

ORD record
ord-b0dc963137524d479f1009c36f165783
Source dataset
uspto-grants-2014_12
Patent number
US08901342B2

Reaction notes

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