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

HRID 131269

Reaction equation

HRID 131269 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (610 mg) in N,N-dimethylformamide (20 mL) is added successively 2-dimethylaminoethyl chloride hydrochloride (1.08 g) and potassium carbonate (2.0 g), and the mixture is stirred at room temperature for 18 hours. To the reaction mixture is added ethyl acetate, and the mixture is washed with water and saturated brine and dried over anhydrous sodium sulfate. The resultant crude product is purified by column chromatography in silica gel (Solvent; chloroform:methanol=20:1→10:1) to give 4-[2-(dimethylamino)-ethoxy]benzaldehyde (640 mg, yield; 66%) as a pale yellow oil. MS (APCI) m/z: 194 [M+H]+

Workup

  1. washthe mixture is washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe resultant crude product is purified by column chromatography in silica gel (Solvent; chloroform:methanol=20:1→10:1)

Sources & evidence

ORD record
ord-9b8e0dd81b794860b5609ed7b69b1ab2
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Linked notes

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