Syringaldehyde → Benzaldehyde, 3,5-dimethoxy-4-[(4-nitrophenyl)methoxy]-

HRID 1109651Notes

Reaction equation

HRID 1109651 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:10][C:9]1[CH:12]=[C:2]([CH:3]=[C:4]([O:5][CH3:6])[C:7]=1[O:8][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=1)[CH:1]=[O:13]

Participants

5

Reactant 3

HCID 8655SyringaldehydeHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 11130915Benzaldehyde, 3,5-dimethoxy-4-[(4-nitrophenyl)methoxy]-Yield 95.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of syringaldehyde (10 g, 55 mmol), p-nitrobenzyl bromide (13 g, 60 mmol) and potassium carbonate (9.0 g, 65 mmol) in 40 ml of acetone was heated under reflux for 4 hours. The solvent was distilled off under reduced pressure. The residue was added with water and then with dichloromethane. The organic layer was thereafter dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was added with ether, followed by stirring at room temperature. The insoluble colorless solid was collected by filtration to give 16.7 g of the title compound (yield: 93%).

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionThe residue was added with water
  4. dry with materialThe organic layer was thereafter dried over anhydrous magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent
  7. additionwas added with ether
  8. filtrationThe insoluble colorless solid was collected by filtration

Sources & evidence

ORD record
ord-d761d8ac78ac496b890fda7f77b02d5e
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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