Water → HCID 23160726, compound

HRID 131267Notes

Reaction equation

HRID 131267 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 23160726HCID 23160726, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 4-hydroxybenzoate (15.3 g) in N,N-dimethylformamide (150 mL) is added successively 2-dimethylaminoethyl chloride hydrochloride (15.9 g) and potassium carbonate (43.2 g) and the mixture is stirred at 110° C. overnight. To the reaction mixture is added water and the mixture is extracted with ethyl acetate. The organic layer is washed successively with a saturated sodium hydrogencarbonate solution and water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant crude product is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=10:1) to give ethyl 4-[2-(dimethylamino)ethoxy]benzoate (14.1 g, yield; 65%) as a brown oil. MS (APCI) m/z: 238 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed successively with a saturated sodium hydrogencarbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude product is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-954a222fbc1c49a39a24154ba27e88c3
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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