4-Hydroxybenzoic Acid → 4-(Octyloxy)benzoic acid

HRID 854224Notes

Reaction equation

HRID 854224 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(O)C.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O>[CH2:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 702EthanolHCID 81401-BromooctaneHCID 14797Potassium Hydroxide2×

Product 1

HCID 172314-(Octyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.64 g (128 mmol) of 4-hydroxybenzoic acid (Aldrich, purity 99%) and 14.32 g (255 mmol) of potassium hydroxide are dissolved in 30 ml of distilled water and added to 260 ml of ethanol. After addition of 33.0 g (29.7 ml, 0.17 mol) of 1-bromooctane (Aldrich, purity 99%), the solution is heated at the boil for 24 hours with stirring. A further 14.32 g (255 mmol) of potassium hydroxide are then added, and the mixture is refluxed with stirring for a further two hours. After the reaction batch has been cooled, the solvent is substantially removed under reduced pressure, and the residue is taken up in distilled water and strongly acidified using 2 M hydrochloric acid solution. The residue is extracted with chloroform, dried over magnesium sulfate, evaporated and recrystallized from acetone.

Workup

  1. temperaturethe solution is heated at the boil for 24 hours
  2. temperaturethe mixture is refluxed
  3. stirringwith stirring for a further two hours
  4. temperatureAfter the reaction batch has been cooled
  5. customthe solvent is substantially removed under reduced pressure
  6. extractionThe residue is extracted with chloroform
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customrecrystallized from acetone

Sources & evidence

ORD record
ord-11a62cb7b3a04cee8d72191643056d8f
Source dataset
uspto-grants-2007_08
Patent number
US07258902B2

Reaction notes

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