Ethanol → Ethyl 3-methylbenzoylformate

HRID 885537

反応式

HRID 885537 の反応式
[Se](=O)=[O:2].Br[CH2:5][C:6]([C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)=[O:7].[CH2:15]([OH:17])[CH3:16]>>[CH3:14][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[C:5]([O:17][CH2:15][CH3:16])=[O:2])[CH:13]=[CH:12][CH:11]=1

参加物

4

反応物 3

HCID 702EthanolHCID 24007Selenium DioxideHCID 100361292-Bromo-1-(3-methylphenyl)ethan-1-one

生成物 1

HCID 2758871Ethyl 3-methylbenzoylformate収率 81%

実験手順

A suspension of selenium dioxide (6.82 g, 61.4 mmol) in ethanol (60 mL) was refluxed for 10 minutes and then, 2-bromo-1-m-tolylethanone (13.1 g, 61.4 mmol) was added. The mixture was refluxed overnight. The cooled reaction was filtered through Celite and the solvent removed under reduced pressure. The residue was diluted with methylene chloride (50 mL), washed with water (2×25 mL), dried (Na2SO4), and concentrated. Purification by column chromatography with silica gel using methylene chloride as eluent gave the title compound (9.6 g, 81%) as oil.

後処理

  1. temperaturewas refluxed for 10 minutes
  2. temperatureThe mixture was refluxed overnight
  3. customThe cooled reaction
  4. filtrationwas filtered through Celite
  5. customthe solvent removed under reduced pressure
  6. additionThe residue was diluted with methylene chloride (50 mL)
  7. washwashed with water (2×25 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customPurification by column chromatography with silica gel

出典と根拠

ORDレコード
ord-1d9b4f61fcf74a8d88dd89ea17c945c6
出典データセット
uspto-grants-2012_08
特許番号
US08242177B2

関連ノート

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