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

HRID 5895

Reaction equation

HRID 5895 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-a122cc9a717e46b8bd8eec79a39f674d
Source dataset
uspto-grants-1993_09
Patent number
US05246943

Linked notes

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