Dimethylformamide → 3-Nitrophenoxyacetic acid methyl ester

HRID 414872Notes

Reaction equation

HRID 414872 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+].[CH3:22][O:23][C:24](=[O:27])[CH2:25]Cl>O>[CH3:22][O:23][C:24](=[O:27])[CH2:25][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7295Methyl chloroacetateHCID 10340Sodium CarbonateHCID 111373-Nitrophenol

Product 1

HCID 107037043-Nitrophenoxyacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

300 g of 3-nitrophenol are added to 800 ml of DMF. Then 240 g of sodium carbonate are added portionwise. Subsequently 270 g of chloroacetic acid methylester is added at 22° C. Then the mixture is stirred at 85° C. for six hours. After being cooled down to 25° C. it is given to 3 kg of water and 1 kg of ice. The resulting suspension is filtered off. The filter cake is washed with 300 g of water and dried in vacuum. Yield: 407 g.

Workup

  1. temperatureAfter being cooled down to 25° C. it
  2. filtrationThe resulting suspension is filtered off
  3. washThe filter cake is washed with 300 g of water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-59738f8d68634a47b39d281b95697ed6
Source dataset
uspto-grants-2012_01
Patent number
US08088182B2

Reaction notes

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