4-Nitrophenol → 1-chloroethyl (4-nitrophenyl) Carbonate

HRID 54820Notes

Reaction equation

HRID 54820 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.N1C=CC=CC=1.Cl[C:18]([O:20][CH:21]([Cl:23])[CH3:22])=[O:19]>C(Cl)(Cl)Cl>[C:18](=[O:19])([O:10][C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)[O:20][CH:21]([Cl:23])[CH3:22]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 105383541-chloroethyl (4-nitrophenyl) CarbonateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a ice cooled mixture of 27.8 g of p-nitrophenol, 16.0 g of pyridine and 1 L of chloroform is added, dropwise, 34 g of alpha-chloroethyl chloroformate. After 1 hour, the ice bath is removed and the reaction is stirred for 16 hours at room temperature. The mixture is washed with water, 0.5% sodium hydroxide and water. The organic layer is dried and concentrated in vacuo to give 47.85 g of the desired product.

Workup

  1. additionis added
  2. customthe ice bath is removed
  3. washThe mixture is washed with water, 0.5% sodium hydroxide and water
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95be3ae76d3f461393cc4b99308b1bd0
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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