4-Nitrophenol → Ethyl 2-(4-nitrophenoxy)acetate

HRID 1604325Notes

Reaction equation

HRID 1604325 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

125.4 g (0.9 mol) of 4-nitrophenol are dissolved in 1000 ml of absolute dimethylformamide and, after addition of 150.6 g (0.9 mol) of dried potassium carbonate, the solution is stirred at room temperature for 45 minutes. 150.6 g=100 ml (0.9 mol) of ethyl bromoacetate are then added dropwise with stirring and the suspension is then heated at an oil bath temperature of 80° C. for 5 hours. The heating is switched off and the suspension is stirred for a further 15 hours, the reaction mixture slowly coming to room temperature. The undissolved inorganic salts are filtered off with suction and the filtrate is concentrated to dryness in vacuo. The residue is partitioned between ethyl acetate and water. The organic phase is extracted with water a further 2 times and then dried over sodium sulphate, filtered and concentrated. The residue is triturated with petroleum ether and filtered off with suction. 192.0 g (95% of theory) of the desired product are obtained, which is processed further without further purification.

Workup

  1. stirringwith stirring
  2. temperaturethe suspension is then heated at an oil bath temperature of 80° C. for 5 hours
  3. stirringthe suspension is stirred for a further 15 hours
  4. customslowly coming to room temperature
  5. filtrationThe undissolved inorganic salts are filtered off with suction
  6. concentrationthe filtrate is concentrated to dryness in vacuo
  7. customThe residue is partitioned between ethyl acetate and water
  8. extractionThe organic phase is extracted with water a further 2 times
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is triturated with petroleum ether
  13. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-0babe810901441da8107080c37e290aa
Source dataset
uspto-grants-1999_11
Patent number
US05994356

Reaction notes

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