o-Vanillin → Benzaldehyde, 3-methoxy-2-(4-nitrophenoxy)-

HRID 2395843

Reaction equation

HRID 2395843 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[O:11]=[CH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:16]([O:17][CH3:18])[C:14]=1[OH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:18][O:17][C:16]1[C:14]([O:15][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[C:13]([CH:21]=[CH:20][CH:19]=1)[CH:12]=[O:11]

Participants

5

Reactant 3

HCID 8991o-VanillinHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 22402430Benzaldehyde, 3-methoxy-2-(4-nitrophenoxy)-Yield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 14.10 g (0.10 mole) of 4-fluoronitrobenzene, 16.40 g (0.10 mole) of o-vanillin, 30 g of powdered potassium carbonate, and 40 mL of DMF is heated with stirring to the boiling point. After 10 minutes the mixture is cooled to 100° C. and 300 mL of ice water is added. Petroleum ether (200 mL) is added and the entire mixture is filtered and the cake is washed with 200 mL of water and then 200 mL of petroleum ether. The damp cake is slurried in 100 mL of methanol and filtered; wt 19.50 g (71% yield); mp 130-131° C.; mass spectrum (DEI), 273 (M+).

Workup

  1. temperatureis heated
  2. filtrationthe entire mixture is filtered
  3. washthe cake is washed with 200 mL of water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-262f8dee2e44442f9798b5e56945b529
Source dataset
uspto-grants-1996_02
Patent number
US05489686

Linked notes

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