Reaction #502054

ord-59738f8d68634a47b39d281b95697ed6

Reaction equation

COC(=O)CCl
chloroacetic acid methylester
O=[N+]([O-])c1cccc(O)c1
3-nitrophenol
CN(C)C=O
DMF
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
COC(=O)COc1cccc([N+](=O)[O-])c1
3-Nitrophenoxyacetic acid methylester

Reactants

COC(=O)CCl
chloroacetic acid methylester
—
ice
O=[N+]([O-])c1cccc(O)c1
3-nitrophenol
CN(C)C=O
DMF
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reagents

None

Solvents

O
water

Conditions

Temperature
85°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter being cooled down to 25° C. it
  2. 2
    FiltrationThe resulting suspension is filtered off
  3. 3
    WashThe filter cake is washed with 300 g of water
  4. 4
    Otherdried in vacuum

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088182B2uspto-grants-2012_01