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

HRID 567095Notes

Reaction equation

HRID 567095 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.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23].O>CN(C)C=O.C(OCC)(=O)C>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][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

7

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×

Product 1

HCID 14638321Methyl 4-(2-(dimethylamino)ethoxy)benzoateYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-hydroxybenzoate (10 g, 66 mmoles) was dissolved in N,N-dimethylformamide (200 mL). Potassium carbonate (45 g, 0.33 moles) and 2-chloro-N,N-dimethylethylamine hydrochloride (14.2 g, 99 mmoles) were added and the resulting mixture was stirred vigorously at room temperature for 7 days. More 2-chloro-N,N-dimethylethylamine hydrochloride (3 g, 20 mmoles) was added and stirring at room temperature was continued for 2 days. The reaction mixture was poured into water (600 mL) and extraction with ethyl acetate (2×200 mL), washing of the combined organic phases with water (200 mL), drying over MgSO4 and evaporation afforded 11.9 g (81%) of methyl 4-(2-dimethylaminoethoxy)benzoate as an oil.

Workup

  1. stirringstirring at room temperature
  2. waitwas continued for 2 days
  3. washwashing of the combined organic phases with water (200 mL)
  4. dry with materialdrying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-e1c21831be3c4640a3dcd3004b69b534
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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