Salicylaldehyde → 2-Propoxy-benzaldehyde

HRID 1169486Notes

Reaction equation

HRID 1169486 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:11][CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:11]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 6998SalicylaldehydeHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2498072-Propoxy-benzaldehydeYield 94.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To salicylaldehyde (12.2 g) dissolved in DMF (100 ml) were added 1-bromopropane (14.7 g) and potassium carbonate (20.7 g), and the resulting mixture was stirred at room temperature for 21.5 hours. The reaction mixture was diluted with ethyl acetate and washed with water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 2-propoxybenzaldehyde (15.47 g) as an oil.

Workup

  1. washwashed with water
  2. dry with materialan aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate
  3. customThe resulting organic layer was evaporated under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-3227d13c76b640c89f43f76e8ec75732
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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