Water → Methyl 4-(2-(dimethylamino)ethoxy)benzoate

HRID 1108614Notes

Reaction equation

HRID 1108614 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 14638321Methyl 4-(2-(dimethylamino)ethoxy)benzoateYield 30.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.52 g (10 mmol) of methyl 4-hydroxybenzoate was dissolved in 40 ml of N,N-dimethylformamide and 2.16 g (15 mmol) of 2-dimethylaminoethyl chloride hydrochloride and 4.15 g (30 mmol) of potassium carbonate were further added. The mixture was heated at 80° C. and stirred overnight. After cooling, water was added to the reaction mixture, the obtained mixture was extracted twice with ethyl acetate, and the extract was washed with brine. The organic phase was dried (Na2SO4) and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=70:1 to 15:1 (v/v)) to obtain 0.69 g (3.09 mmol) of methyl 4-(2-dimethylaminoethoxy)benzoate as a pale brown oily substance. Its spectroscopic data are as follows:

Workup

  1. temperatureAfter cooling
  2. extractionthe obtained mixture was extracted twice with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=70:1 to 15:1 (v/v))

Sources & evidence

ORD record
ord-9a9c1be741f044d582743a920e9494d0
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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