4-Nitrophenol → Isopropenyl p-nitrophenyl carbonate

HRID 2185741Notes

Reaction equation

HRID 2185741 reaction equation
Cl[C:2]([O:4][C:5]([CH3:7])=[CH2:6])=[O:3].[CH:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10]([OH:17])[CH:9]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:2](=[O:3])([O:17][C:10]1[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[CH:8][CH:9]=1)[O:4][C:5]([CH3:7])=[CH2:6]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 93846Isopropenyl chloroformate

Product 1

HCID 22271989Isopropenyl p-nitrophenyl carbonateYield 84.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Isopropenyl chloroformate (5.0 g, 41.5 mmol) was added to an ice cold suspension of p-nitrophenol (6.3 g, 45.6 mmol) in chloroform (100 mL). To the stirred reaction mixture, pyridine (3.32 g, 41.5 mmol) was added dropwise over 20 minutes. After stirring at ice bath temperature for 15 minutes, the reaction mixture was allowed to warm up and stirred at room temperature for 16 hours. The reaction mixture was washed with water, 1N HCl, ice-cold 1% aqueous sodium hydroxide, water and brine. The organic layer was dried (MgSO4) and the solvent was evaporated. The solid residue was subsequently crystallized from hexane to provide the title compound (7.8 g, 84% yield): 1H NMR (CDCl3, 300 MHz) δ2.05 (s, 3H), 4.82 (t, 1H, J=1.0 Hz), 4.96 (d, 1H, J=2.0 Hz), 7.40-7.46 (m, 2H), 8.27-8.32 (m, 2H).

Workup

  1. additionwas added dropwise over 20 minutes
  2. temperatureto warm up
  3. stirringstirred at room temperature for 16 hours
  4. washThe reaction mixture was washed with water, 1N HCl, ice-cold 1% aqueous sodium hydroxide, water and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe solid residue was subsequently crystallized from hexane

Sources & evidence

ORD record
ord-f74a7377b5be4e3791fb9582745f25f6
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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