Nitromethane → Methyl 4-formyl-2-methoxybenzoate

HRID 59315Notes

Reaction equation

HRID 59315 reaction equation
C[O-:2].[Na+].[N+](C)([O-])=O.Br[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([O:20][CH3:21])[CH:11]=1>CO>[CH:9]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([O:20][CH3:21])[CH:11]=1)=[O:2]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 10942334Sodium MethoxideHCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Product 1

HCID 18510332Methyl 4-formyl-2-methoxybenzoateYield 641%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium methoxide (0.260 g, 4.82 mmol) in methanol (200 mL) was added nitromethane (4.03 g, 11.58 mmol) under nitrogen atmosphere and the reaction mixture was stirred and reflux for 30 minutes. Methyl 4-(bromomethyl)-2-methoxybenzoate (10.00 g, 9.65 mmol) in methanol was added and the reaction mixture was refluxed for 7-8 h. The reaction mass was concentrated and diluted with CHCl3. The diluted reaction mass was washed with 2N NaOH solution. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 6.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.83 (m, 6H), 7.36 (d, J=6.6 Hz, 2H), 7.79 (d, J=7.8 Hz, 1H), 10.04 (s, 1H).

Workup

  1. temperaturereflux for 30 minutes
  2. temperaturethe reaction mixture was refluxed for 7-8 h
  3. concentrationThe reaction mass was concentrated
  4. additiondiluted with CHCl3
  5. customThe diluted reaction mass
  6. washwas washed with 2N NaOH solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8135556d67a7411db9c242346f41abc8
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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