Methyl iodide → 1,2,3,4-Tetramethoxybenzene

HRID 1527670

反応式

HRID 1527670 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[OH:13].[C:14]([O-])([O-])=O.[K+].[K+].CI.CCOC(C)=O>CC(C)=O>[CH3:12][O:11][C:7]1[CH:6]=[CH:5][C:4]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6035772,3,4-Trimethoxyphenol

生成物 1

HCID 6077731,2,3,4-Tetramethoxybenzene収率 82.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Following the procedure by Tremblay et al.,17 17 (3.851 g, 20.9 mmol) was dissolved in dry acetone (90.0 ml), and K2CO3 (9.36 g, 67.7 mmol) was added followed by MeI (9.0 mL, 144 mmol). The reaction was heated under reflux for 26 h and monitored by TLC (1:9 EtOAc:hexanes) for completion. When complete the reaction was cooled to room temperature and filtered. The acetone was removed under reduced pressure and the residue was taken up in CH2Cl2 (50 mL). The suspension was filtered, dried over MgSO4, filtered again, and condensed. The crude product can be purified by flash chromatography (1:4 EtOAc:hexanes), however, recrystallization from Et2O/hexanes was sufficient to provide pure 18 (3.405 g, 17.2 mmol, 82%) as white needles.

後処理

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 26 h
  3. filtrationfiltered
  4. customThe acetone was removed under reduced pressure
  5. filtrationThe suspension was filtered
  6. dry with materialdried over MgSO4
  7. filtrationfiltered again
  8. customcondensed
  9. customThe crude product can be purified by flash chromatography (1:4 EtOAc:hexanes)
  10. customhowever, recrystallization from Et2O/hexanes

出典と根拠

ORDレコード
ord-160a9da54c0247b199edd594e23558a2
出典データセット
uspto-grants-2015_07
特許番号
US09089605B2

関連ノート

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