Salicylaldehyde → 2-(Benzyloxy)benzaldehyde

HRID 394900Notes

Reaction equation

HRID 394900 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7](=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH:7]=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 3447842-(Benzyloxy)benzaldehydeYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

185 g of dimethylformamide and 82.8 g (0.6 mol) of potassium carbonate were placed in a flask, and 61 g (0.5 mol) of salicylaldehyde were added dropwise thereto. 75.9 g (0.6 mol) of benzyl chloride were then added dropwise to the resulting mixture at a temperature of 50° C. for one hour. After the addition, the mixture was stirred at a temperature of 70° C. for two hours. The resulting reaction mixture was washed with 185 g of toluene and 330 g of water. The solvent was distilled out of the mixture at an inside temperature of 90° C. under a reduced pressure of 10 mmHg thereby providing 104.5 g of 2-benzyloxybenzaldehyde as bottom in the form of brown liquid having a purity 97.9% in a yield of 96.5%.

Workup

  1. additionAfter the addition
  2. customThe resulting reaction mixture
  3. washwas washed with 185 g of toluene and 330 g of water
  4. distillationThe solvent was distilled out of the mixture at an inside temperature of 90° C. under a reduced pressure of 10 mmHg

Sources & evidence

ORD record
ord-55ab40287c4c409cb34390050411be0a
Source dataset
uspto-grants-2003_08
Patent number
US06603029B1

Reaction notes

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