4-Nitrophenol → Isopropenyl p-nitrophenyl carbonate

HRID 2292588Notes

Reaction equation

HRID 2292588 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 carbonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Isopropenyl chloroformate (5.0 g) was added to an ice cold suspension of p-nitrophenol in chloroform (100 mL). To the stirred reaction mixture, pyridine (3.32 g) 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 overnight. The reaction mixture was washed with water, IN HCl, ice-cold 1% aqueous sodium hydroxide, water and brine. The organic layer was dried over sodium sulfate and evaporated. The solid residue weighed at 8.7 g. It was crystallized from benzene-hexane m.p. 71-72° . 1H NMR (CDCl3) δ 2.05 (3H, s), 4.82 (2H, s), 7.44 (2H, d) and 8.01 (2H, d); 13C NMR (CDCl3) δ19.59, 102.49, 128.25, 128.79, 131.29, 139.8, 153.07 and 163.84; 1R (KBr) 1770, 1521, 1352, 1266, 1207, 859 cm-1.

Workup

  1. additionwas added dropwise over 20 minutes
  2. temperatureto warm up
  3. stirringstirred at room temperature overnight
  4. washThe reaction mixture was washed with water, IN HCl
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customIt was crystallized from benzene-hexane m.p. 71-72°

Sources & evidence

ORD record
ord-74370d5811724c5cb925d22318db6e40
Source dataset
uspto-grants-1997_11
Patent number
US05684018

Reaction notes

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