Methyl morpholine oxide → Ethyl 4-formyl-3-nitrobenzoate

HRID 969275Notes

Reaction equation

HRID 969275 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].C[N+]1([O-])CC[O:21]CC1>C(#N)C>[CH:2]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15])=[O:21]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 13685261Ethyl 4-(bromomethyl)-3-nitrobenzoate

Product 1

HCID 18001104Ethyl 4-formyl-3-nitrobenzoateYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-bromomethyl-3-nitrobenzoate (46.11 g) was dissolved in 500 ml of acetonitrile, then 20 g of 4-methylmorpholine-N-oxide was added and the mixture was stirred at room temperature for 80 minutes. The reaction solution was concentrated in vacuo, water was added and the mixture was extracted with chloroform. The organic layer was washed with a saturate aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (4:1) as an eluting solvent to give 10.723 g of ethyl 4-formyl-3-nitrobenzoate.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with a saturate aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7e65d3d5473a4f3597b42fe4eba7d07c
Source dataset
uspto-grants-2007_12
Patent number
US07307074B2

Reaction notes

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