Vanillin → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 394901Notes

Reaction equation

HRID 394901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

76 g (0.5 mol) of 3-methoxy-4-hydroxybenzaldehyde were placed in a four-necked flask together with 228 g of dimethylformamide and 82.8 g (0.6 mol) of potassium carbonate. 66.4 g (0.525 mol) of benzyl chloride was added dropwise at a temperature of 60° C. for one hour. After the addition, the mixture was stirred at a temperature of 60° C. for five hours. The resulting reaction mixture was washed with 190 g of toluene and 330 g of water. 270 g of the solvent were removed by distillation under reduced pressure of 70 mmHg and then 265 g of n-heptane and 80 g of toluene were added to the distillation residue and the separated crystals were collected by filtration to provide 102.6 g of 3-methoxy-4-benzyloxybenzaldehyde as white crystals in a yield of 84.8%.

Workup

  1. additionAfter the addition
  2. customThe resulting reaction mixture
  3. washwas washed with 190 g of toluene and 330 g of water
  4. custom270 g of the solvent were removed by distillation under reduced pressure of 70 mmHg
  5. addition265 g of n-heptane and 80 g of toluene were added to the distillation residue
  6. filtrationthe separated crystals were collected by filtration

Sources & evidence

ORD record
ord-79e6bfb2b17c46a3bc3102bfec2fe9a9
Source dataset
uspto-grants-2003_08
Patent number
US06603029B1

Reaction notes

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