Chloroacetic Acid → 2-(2-(Benzyloxy)ethoxy)acetic acid

HRID 506408Notes

Reaction equation

HRID 506408 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:15][C:16]([OH:18])=[O:17]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:15][C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydride

Product 1

HCID 217901362-(2-(Benzyloxy)ethoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(Benzyloxy)ethanol (0.75 ml) is dissolved in N,N-dimethylformamide (3 ml), and added dropwise to a solution of sodium hydride (400 mg) in N,N-dimethylformamide under ice-cooling. The mixture is stirred for 40 minutes. To the reaction solution is added chloroacetic acid (500 mg) under ice-cooling, and the mixture is stirred at room temperature for 1 day. To the reaction solution is added ice-water, and the mixture is extracted with ethyl acetate. To the aqueous layer is added 6N HCl, and the solution is adjusted to pH 2 and extracted with ethyl acetate. The organic layer is washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure to give 2-(benzyloxy)ethoxy acetic acid (895 mg). MS (m/z): 211 [M+H]+.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature for 1 day
  4. extractionthe mixture is extracted with ethyl acetate
  5. additionTo the aqueous layer is added 6N HCl
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0bb1d47ff2bf4ff3a18de9a30536ace5
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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