Water → 4-(Benzyloxy)-3-methoxybenzaldehyde

HRID 1780012Notes

Reaction equation

HRID 1780012 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

100 g of 4-hydroxy-3-methoxybenzaldehyde was dissolved in 700 ml of dimethylformamide, further 100 g of anhydrous potassium carbonate and 90 ml of benzyl bromide were added thereto, and the mixture was stirred for 1.5 hours at 80° C. After the completion of the reaction, the reaction solution was poured into 1 liter of water and extracted with 300 ml of ethyl acetate three times. The ethyl acetate layer was washed with water twice and dried over anhydrous magnesium sulfate and then concentrated. The residue obtained was crystallized from methanol, affording 142.95 g of 4-benzyloxy-3-methoxybenzaldehyde (89% yield).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with 300 ml of ethyl acetate three times
  3. washThe ethyl acetate layer was washed with water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customwas crystallized from methanol

Sources & evidence

ORD record
ord-6ae3bb9713af4f6696bf8206a25c08cd
Source dataset
uspto-grants-1997_05
Patent number
US05629340

Reaction notes

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