Methyl iodide → Methyl 4-tert-butylphenylisobutyric acid

HRID 343756노트

반응식

HRID 343756 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[CH3:17].[H-].[Na+].[CH2:20]1COC[CH2:21]1>>[CH3:20][CH2:21][C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)([CH3:17])[C:12]([OH:14])=[O:13]

참가 물질

5

반응물 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 605629Methyl p-tert-butylphenylacetate

생성물 1

HCID 67601534Methyl 4-tert-butylphenylisobutyric acid

실험 절차

A solution of methyl 4-tert-butylphenylacetate (30.00 g, 0.145 mol) and iodomethane (45.41 g, 0.320 mol) in 125 mL of dry THF was added to a slurry of NaH (8.72 g, 0.363 mol) in 200 mL of THF dropwise over 30 minutes. After completion of the addition, the reaction mixture was heated at reflux for 1.5 hr. The reaction was allowed to cool to room temperature, filtered through Celite and concentrated. The residue was diluted in ether, washed with H2O, and dried over MgSO4. Evaporation of the solvent afforded the desired product as an oil. A mixture of the crude methyl 4-tert-butylphenylisobutyrate and 4:1 EtOH/H2O containing KOH (10.07 g, 0.179 mol) were heated to reflux for 4 hr. The EtOH was evaporated in vacuo, the residual solution was acidified to pH 2 with 2N HCl, and the precipitated solid filtered. The white solid was the dried (60° C., 1 mm Hg, 24 hr) to give the desired product (23.45 g, 73.2% from methyl 4-tert-butylphenylacetate). 1H NMR (CDCl3) 1.34 (s, 9H), 1.62 (s, 6H), 7.37 (s, 4H), 11.4-12.4 (brs, 1H). 13C NMR (CDCl3) 26.16, 31.30, 34.35, 45.81, 125.31, 125.48, 140.64, 149.66, 183.57.

후처리

  1. additionAfter completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 1.5 hr
  4. filtrationfiltered through Celite
  5. concentrationconcentrated
  6. additionThe residue was diluted in ether
  7. washwashed with H2O
  8. dry with materialdried over MgSO4
  9. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-7445580493ce4bee8aa06048b2af70e9
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863899

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