Hydrochloric Acid → (4-Octylphenyl)acetic acid

HRID 653821Notes

Reaction equation

HRID 653821 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12](CC(N2CCOCC2)=S)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:24]([OH:26])[CH3:25].[OH-:27].[K+].Cl>C(OCC)(=O)C.O>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:25][C:24]([OH:27])=[O:26])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 14817236HCID 14817236, compound

Product 1

HCID 12387347(4-Octylphenyl)acetic acidYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

117 g of the 4-[2-(4-octylphenyl)-1-thioxoethyl]-morpholine was added to 250 ml of ethanol and dissolved therein. 50 ml of water and 46.3 g of potassium hydroxide were added to the obtained solution and the mixture was refluxed for three hours and then allowed to cool to room temperature. Then 10% hydrochloric acid was added thereto by portions until the mixture became acidic. After adding 500 ml of ethyl acetate, the organic layer was washed with water until the aqueous layer became neutral. The organic layer was separated and the solvent was distilled off. To the residue, were added 500 ml of triethylene glycol, 70 ml of water and 77.2 g of potassium hydroxide and the resulting mixture was refluxed for four hours. After allowing to cool to room temperature, 10% hydrochloric acid was added thereto by portions until it became acidic. After adding 500 ml of ethyl acetate, the organic layer was washed with water until the aqueous layer became neutral. The organic layer was separated and dehydrated over anhydrous sodium sulfate. The solvent was distilled off and the residue was recrystallized from hexane. Thus 65.5 g of p-octylphenylacetic acid was obtained. Yield: 74%.

Workup

  1. dissolutiondissolved
  2. temperaturethe mixture was refluxed for three hours
  3. washthe organic layer was washed with water until the aqueous layer
  4. customThe organic layer was separated
  5. distillationthe solvent was distilled off
  6. additionTo the residue, were added 500 ml of triethylene glycol, 70 ml of water and 77.2 g of potassium hydroxide
  7. temperaturethe resulting mixture was refluxed for four hours
  8. temperatureto cool to room temperature
  9. addition10% hydrochloric acid was added
  10. additionAfter adding 500 ml of ethyl acetate
  11. washthe organic layer was washed with water until the aqueous layer
  12. customThe organic layer was separated
  13. distillationThe solvent was distilled off
  14. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-edfd7aa3e92c49b8ada0ff6269229f09
Source dataset
uspto-grants-1992_07
Patent number
US05128472

Reaction notes

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