3-Hydroxybenzaldehyde → 2-Propoxy-benzaldehyde

HRID 1169492Notes

Reaction equation

HRID 1169492 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][CH2:12][CH3:13].C(=O)([O-])[O-:15].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:11]([O:15][C:7]1[CH:8]=[CH:9][CH:2]=[CH:3][C:4]=1[CH:5]=[O:6])[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2498072-Propoxy-benzaldehydeYield 98.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-hydroxybenzaldehyde (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 17 hours. The reaction mixture was diluted with ethyl acetate and washed respectively 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 (16.18 g) as an oil.

Workup

  1. washwashed respectively 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-dd0921ddbc1e45e6b9a002e194932033
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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