4-Hydroxybenzoic Acid → Benzoic acid, 2-(dodecyloxy)-

HRID 247800Notes

Reaction equation

HRID 247800 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-:25].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)C>[CH2:1]([O:25][C:22]1[CH:23]=[CH:15][CH:16]=[CH:17][C:18]=1[C:19]([OH:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Product 1

HCID 289454Benzoic acid, 2-(dodecyloxy)-

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of dodecylbromide (8.2 g, 4-hydroxybenzoic acid (5 g) and potassium carbonate (5 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. Diethyl ether was added in order to effect extraction and the extracted layer was distilled to remove the solvent. The residue was added to a solution of sodium hydroxide (3 g). water (10 ml) and ethanol(50 ml) and the solution was refluxed for about one day. The solution was neutralized with dilute aqueous hydrochloric acid solution and distilled to remove the solvent and concentrated. Solid collected was recrystallized from water/ethanol to obtain the titled compound (4.9 g).

Workup

  1. extractionextraction
  2. distillationthe extracted layer was distilled
  3. customto remove the solvent
  4. additionThe residue was added to a solution of sodium hydroxide (3 g)
  5. temperaturewater (10 ml) and ethanol(50 ml) and the solution was refluxed for about one day
  6. distillationdistilled
  7. customto remove the solvent
  8. concentrationconcentrated
  9. customSolid collected
  10. customwas recrystallized from water/ethanol

Sources & evidence

ORD record
ord-2515ebd924874b8ba0035998e527f816
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Reaction notes

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