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

HRID 1401740Notes

Reaction equation

HRID 1401740 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 to 125° C. in 300 ml of xylene, and 69.1 g (0.5 mol) of 4-hydroxybenzoic acid were introduced in portions over the course of six hours. The batch was subsequently stirred at 125° C. for one hour, cooled to room temperature, and filtered with suction, and the solid 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. temperaturecooled to room temperature
  2. filtrationfiltered with suction
  3. washthe solid product was washed three times with 45 ml of xylene
  4. customThe yield
  5. customafter drying under reduced pressure at 100° C.

Sources & evidence

ORD record
ord-8f569fe39dd24224843fa1e781b1eaf2
Source dataset
uspto-grants-2014_12
Patent number
US08907118B2

Reaction notes

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