4-Nitrophenol → HCID 53827701, compound

HRID 581838Notes

Reaction equation

HRID 581838 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][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CN(C)C=O.CCOCC>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 53827701HCID 53827701, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

27.6 g (0.2 mol) of 4-nitrophenol are dissolved in 300 ml of dimethylformamide and, after addition of 27.6 g (0.2 mol) of dried potassium carbonate, the mixture is stirred at room temperature for 45 minutes. Thereafter, 50.4 g (0.22 mol=34.9 ml) of benzyl bromoacetate are added dropwise, while stirring, and the suspension is then heated at 80° C. (oil bath temperature) for 5 hours. The oil bath is then switched off and the suspension is stirred for a further 15 hours, during which the reaction mixture slowly comes to room temperature. The undissolved inorganic salts are filtered off with suction and the mother liquor is concentrated to dryness in vacuo. The residue is dissolved in methylene chloride and, after washing twice with water, the solution is dried over sodium sulphate, filtered and concentrated. The product obtained is suspended in ether and filtered off with suction. Yield: 55.4 g (96.4% of theory).

Workup

  1. stirringwhile stirring
  2. temperaturethe suspension is then heated at 80° C. (oil bath temperature) for 5 hours
  3. stirringthe suspension is stirred for a further 15 hours, during which the reaction mixture
  4. customslowly comes to room temperature
  5. filtrationThe undissolved inorganic salts are filtered off with suction
  6. concentrationthe mother liquor is concentrated to dryness in vacuo
  7. dissolutionThe residue is dissolved in methylene chloride
  8. washafter washing twice with water
  9. dry with materialthe solution is dried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product obtained
  13. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-e72a93a6458e42389f1a4fe76a688000
Source dataset
uspto-grants-1999_07
Patent number
US05922717

Reaction notes

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