4-Nitrophenol → Ethyl 4-nitrophenyl carbonate

HRID 1796191Notes

Reaction equation

HRID 1796191 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].N1C=CC=CC=1.C(OCC)(=O)C>ClCCl>[C:12](=[O:13])([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[O:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 1049PyridineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformate

Product 1

HCID 586863Ethyl 4-nitrophenyl carbonateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-nitrophenol (1.00 g) in dichloromethane (20 ml) were added dropwise ethyl chloroformate (0.70 ml) and pyridine (0.70 ml) under ice-cooling, and the resulting mixture was stirred at room temperature overnight and then evaporated in vacuo. To the residue obtained was added ethyl acetate, and the organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution, a saturated aqueous sodium chloride solution, a saturated aqueous potassium hydrogensulfate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residual solid obtained was collected by filtration using hexane to afford ethyl 4-nitrophenyl carbonate (1.44 g, yield: 95%) as a white solid.

Workup

  1. temperaturecooling
  2. customevaporated in vacuo
  3. customTo the residue obtained
  4. washthe organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residual solid obtained
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1f796e95d6c7409b88e9c4087a261aa3
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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