Methyl iodide → 2,3,4,5-tetramethoxytoluene

HRID 1527656노트

반응식

HRID 1527656 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:11][CH3:12])[C:3]=1[O:13][CH3:14].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:14][O:13][C:3]1[C:4]([O:11][CH3:12])=[C:5]([O:10][CH3:15])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[CH3:1]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 249755962,3,6-Trimethoxy-4-methylphenol

생성물 1

HCID 98777642,3,4,5-tetramethoxytoluene수율 99%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

According to a modification of the procedure by Brimble et al.,36 11 (0.660 g, 3.33 mmol) and K2CO3 (4.08 g, 29.5 mmol) were added to a flame-dried 250 mL round bottom flask followed by dry acetone (120.0 mL) and MeI (2.0 mL, 32 mmol) at room temperature. A water-jacketed reflux condenser was attached and the reaction was heated under reflux for 12 hours. The reaction was then cooled, filtered, and the solvent was removed under reduced pressure. The brown residue was then resuspended in CH2Cl2, dried over MgSO4, filtered, and condensed. The resulting colorless oil was then purified by flash chromatography (1:9 EtOAc:hexanes) to provide 6 (0.690 g, 3.25 mmol, 99%) as a colorless oil.

후처리

  1. additionwere added to a flame-dried 250 mL round bottom flask
  2. customA water-jacketed reflux condenser was attached
  3. temperaturethe reaction was heated
  4. temperatureunder reflux for 12 hours
  5. temperatureThe reaction was then cooled
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customcondensed
  11. customThe resulting colorless oil was then purified by flash chromatography (1:9 EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-65e884d6238940ba9ddbbe4560a21a9a
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09089605B2

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