4-Nitrophenol → Isopropenyl p-nitrophenyl carbonate

HRID 244368Notes

Reaction equation

HRID 244368 reaction equation
[C:1](=[O:4])([OH:3])[OH:2].[C:5](Cl)([CH3:7])=[CH2:6].[N+:9]([C:12]1[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=1)([O-:11])=[O:10].C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1](=[O:3])([O:2][C:15]1[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=1)[O:4][C:5]([CH3:7])=[CH2:6]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 6212ChloroformHCID 86665012Isopropenyl chloride carbonate

Product 1

HCID 22271989Isopropenyl p-nitrophenyl carbonateYield 17.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To isopropenyl chloride carbonate (6.68 g) were added 4-nitrophenol (5 g) and chloroform (150 ml), and thereto was added drowpise pyridine (2.9 ml) under ice-cooling over a period of 20 minutes. Then, the mixture was stirred under ice-cooling for 15 minutes, then warmed to room temperature, and further stirred overnight. After the reaction was completed, the reaction solution was washed succesively with 1N aqueous hydrochloric acid solution, water and a satureated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1) to give the title compound (1.41 g).

Workup

  1. temperaturecooling over a period of 20 minutes
  2. temperaturecooling for 15 minutes
  3. stirringfurther stirred overnight
  4. washthe reaction solution was washed succesively with 1N aqueous hydrochloric acid solution, water
  5. dry with materiala satureated aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-639b2253bfa746fdab05e32f219bda3e
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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