Ethanol → Ethyl 3-methylbenzoylformate

HRID 1966630Notes

Reaction equation

HRID 1966630 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 2758871Ethyl 3-methylbenzoylformateYield 81%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-644d9207f7d945eaac0117d4e0f413ed
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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