Ethanol → Ethyl 3-methoxybenzoylformate

HRID 1966649Notes

Reaction equation

HRID 1966649 reaction equation
[Se](=O)=[O:2].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:7].[CH2:16]([OH:18])[CH3:17]>>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[C:5]([O:18][CH2:16][CH3:17])=[O:2])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24007Selenium DioxideHCID 101294Bromomethyl 3-methoxyphenyl ketone

Product 1

HCID 2758863Ethyl 3-methoxybenzoylformateYield 53%

Procedure

A suspension of selenium dioxide (4.08 g, 37 mmol) in ethanol (35 mL) was refluxed for 10 minutes and then, Intermediate 65 (8.44 g, 37 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 (4.12 g, 53%) 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-df3ecd2693b84504af0e60417e53918a
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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