Hydrochloric Acid → 1-(2-Methoxy-3-nitrophenyl)ethanone

HRID 629188ノート

反応式

HRID 629188 の反応式
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[C:14](=O)([O-])[O-].[K+].[K+].IC.Cl>CN(C=O)C>[CH3:14][O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2 回HCID 11430Potassium CarbonateHCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

生成物 1

HCID 155794711-(2-Methoxy-3-nitrophenyl)ethanone収率 97.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A slurry of 1-(2-hydroxy-3-nitrophenyl)ethanone (1.00 g, 5.52 mmol) and potassium carbonate (3.05 g, 22.08 mmol) in DMF (20 mL) was stirred at room temperature for 30 minutes, then iodomethane (1.338 mL, 16.56 mmol) was added dropwise and the resulting mixture was allowed to stir at room temperature overnight. LCMS indicated some un-reacted starting material remained, therefore additional iodomethane (1.338 mL, 16.56 mmol) was added and the mixture was warmed to 50° C. over 2 days. Reaction was quenched by the addition of water to give a solution followed by adjusting the pH with 1N HCl to ˜7. The resulting solution was extracted with ethyl acetate (80 mL×3) and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the product, 1-(2-methoxy-3-nitrophenyl)ethanone (1.05 g, 5.38 mmol, 97% yield) as a tan oil. HPLC (Method N) RT=1.86 minutes.

後処理

  1. temperaturethe mixture was warmed to 50° C. over 2 days
  2. customReaction
  3. customwas quenched by the addition of water
  4. customto give a solution
  5. extractionThe resulting solution was extracted with ethyl acetate (80 mL×3)
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-a8dc8e1cda124ce4bd4d084332cec486
出典データセット
uspto-grants-2016_04
特許番号
US09315494B2

反応ノート

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