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

HRID 247798

Reaction equation

HRID 247798 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)C>[CH2:1]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric Acid2×HCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 172314-(Octyloxy)benzoic acidYield 71.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of octylbromide (4.19 g), 4-hydroxybenzoic acid (3 g) and potassium carbonate (3 g) in dimethylformamide (100 ml) was stirred at 130° C. for two hours. The solution was poured in water and neutralized with dilute aqueous hydrochloric acid solution. Diethylether was added to effect extraction. After the extracted layer was distilled to remove the solvent, the residue was added to a solution of sodium hydroxide (3.3 g), water (10 ml) and ethanol (50 ml). The solution obtained was refluxed for about a day and neutralized with dilute aqueous hydrochloric acid solution. The solution was distilled to remove the solvent and concentrated. The solid obtained was collected and recrystallized from water/ethanol to obtain the titled compound (3.88 g).

Workup

  1. distillationAfter the extracted layer was distilled
  2. customto remove the solvent
  3. additionthe residue was added to a solution of sodium hydroxide (3.3 g), water (10 ml) and ethanol (50 ml)
  4. customThe solution obtained
  5. distillationThe solution was distilled
  6. customto remove the solvent
  7. concentrationconcentrated
  8. customThe solid obtained
  9. customwas collected
  10. customrecrystallized from water/ethanol

Sources & evidence

ORD record
ord-4ec4327d040a4a578173b0f6893bc343
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Linked notes

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