Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 1884250Notes

Reaction equation

HRID 1884250 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][C:8]=1[OH:9].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:12]([O:9][C:8]1[CH:7]=[CH:6][C:5]([CH:10]=[O:11])=[CH:4][C:3]=1[O:2][CH3:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

15.2 g (0.1 mol) of vanilline, 20.5 g (0.12 mol) of benzyl bromide, 17.9 g (0.13 mol) of potassium carbonate and 150 ml of N,N-dimethylformamide were mixed and stirred at 50° C. for 2 hours. Water was added to the reaction mixture, which was followed by extracted with ethyl acetate, washed with 5% hydrochloric acid and then saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with hexane and dried to give 23.1 g of 4-benzyloxy-3-methoxybenzaldehyde.

Workup

  1. extractionby extracted with ethyl acetate
  2. washwashed with 5% hydrochloric acid
  3. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. washThe residue was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-918a207132004c508f62f51595761aa7
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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