4-Hydroxybenzaldehyde → p-(2-(Dimethylamino)ethoxy)benzaldehyde

HRID 550959Notes

Reaction equation

HRID 550959 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].[CH3:16][N:17]([CH:19]=O)[CH3:18]>O>[CH3:16][N:17]([CH2:19][CH2:10][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:18]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium Carbonate

Product 1

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (500 mg, 4 mmol) and K2CO3 (662 mg, 4.8 mmol) in anhydrous DMF, N,N-dimethyl-2-metilsulphonilethylamine (775 mg, 4.4 mmol) was added. The reaction mixture was heated to reflux, under magnetic stirring, for 4 hours, then poured in water to obtain a suspension from which the solid was isolated by filtration. The crude product was purified by chromatography on silica gel (ethyl acetate), to give 379 mg of pure product of the title (yield 49%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux, under magnetic stirring, for 4 hours
  3. customto obtain a suspension from which the solid
  4. customwas isolated by filtration
  5. customThe crude product was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-b88a1399b0dd417495c9641aa7d9a78e
Source dataset
uspto-grants-2011_05
Patent number
US07947674B2

Reaction notes

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