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

HRID 1165607

반응식

HRID 1165607 반응식
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]

참가 물질

8

반응물 5

HCID 280Carbon DioxideHCID 77341,4-DiethylbenzeneHCID 84541-MethylpyrrolidineHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8471Triethylamine용매

실험 절차

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 (2.50 M.) (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.

후처리

  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

출처 및 근거

ORD 기록
ord-eae0522acf8448b8b4c8514a5834b326
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910337

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