Carbon Dioxide → 2-(4-Ethylphenyl)propanoic acid

HRID 1089638

Reaction equation

HRID 1089638 reaction equation
CN1CCCC1.CC(C)([O-])C.[K+].[CH2:13]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14].C([Li])CCC.[C:28](=[O:30])=[O:29]>O.C(N(CC)CC)C>[CH2:13]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:22])[C:28]([OH:30])=[O:29])=[CH:17][CH:16]=1)[CH3:14]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 77341,4-DiethylbenzeneHCID 84541-MethylpyrrolidineHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium2×

Product 1

HCID 5278162-(4-Ethylphenyl)propanoic acidYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a mixed solvent of dried 1-methylpyrrolidine (6.0 ml.) and triethylamine (10.0 ml.) were added potassium tertiary-butoxide (11.7 g., 104 mmoles), 4.15 ml. 1,4-diethylbenzene (3.60 g. 26.8 mmoles). The flask was flushed with nitrogen, and the reaction mixture was stirred in an ice-water bath for 15 minutes. n-Butyllithium (2.50M.) (8.0 ml, 20.0 mmoles) was charged dropwise into the flask over a period of 10 minutes. A red suspension developed upon additions of n-butyllithium. The mixture was stirred for 5 hours under ice-water cooling. After completion of the reaction, the reaction mixture was carbonated with 200 ml. of dry-ice inside a dry-box under a nitrogen atmosphere. The resulting white solid mass was then hydrolyzed with water (3 ml.) on the next morning. After removal of all volatile components under vacuum, the solid paste was dissolved in water and washed with pentane. The aqueous layer was acidified with dilute hydrochloric acid and extracted with ether. The combined ether extracts were dried over sodium sulfate, filtered and concentrated to afford 4-ethylphenylpropionic acid (2.76 g., 15.5 moles), corresponding to a yield of 77.5% based on n-butyllithium.

Workup

  1. customThe flask was flushed with nitrogen
  2. stirringThe mixture was stirred for 5 hours under ice-water cooling
  3. customAfter completion of the reaction
  4. customAfter removal of all volatile components under vacuum
  5. dissolutionthe solid paste was dissolved in water
  6. washwashed with pentane
  7. extractionextracted with ether
  8. dry with materialThe combined ether extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-60bb5fab103a45e9a29ba657431e2339
Source dataset
uspto-grants-1992_01
Patent number
US05078906

Linked notes

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