Water → 4-Nitrophenyl propyl carbonate

HRID 2214820Notes

Reaction equation

HRID 2214820 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH3:7])=[O:3].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O-:10])=[O:9].C(N(CC)CC)C.O>C1COCC1>[CH2:5]([O:4][C:2]([O:17][C:14]1[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=1)=[O:3])[CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 7998Propyl chloroformateHCID 8471Triethylamine

Product 1

HCID 544839324-Nitrophenyl propyl carbonateYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of propyl chloroformate (613 mg) in THF (3 ml) was added to a solution of 4-nitrophenol (693 mg) and triethylamine (0.836 ml) in THF (10 ml) at 0° C. After stirred at room temperature for 30 minutes, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous sodium carbonate solution, an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried, and concentrated to obtain the title compound (1.11 g) as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a 10% aqueous sodium carbonate solution
  3. dry with materialan aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1d8845f3ac34e83ac3e979414435afd
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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