Ethanol → Ethyl 3-methylbenzoylformate

HRID 2424841

Reaktionsgleichung

Reaktionsgleichung von HRID 2424841
[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

Komponenten

4

Edukt 3

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

Produkt 1

HCID 2758871Ethyl 3-methylbenzoylformateAusbeute 81 %

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-94c1d67678164f4baedd9b692e3b8f19
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964615B2

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