Water → Butyl 4-nitrophenyl carbonate

HRID 43280

Reaction equation

HRID 43280 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N([CH2:16][CH3:17])CC)C.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])C.O>O1CCCC1.ClC(OCCCC)=O>[C:18](=[O:20])([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[O:21][CH2:22][CH2:23][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 12867351Butyl 4-nitrophenyl carbonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 61140Butyl chloroformateSolvent

Procedure

Into a solution of 3.00 g of 4-nitrophenol and 3.31 mL of triethylamine in 30 mL of tetrahydrofuran, 2.75 mL of butyl chloroformate was dropped under cooling on ice. To the reaction mixture, after stirred at the same temperature for 10 min, ethyl acetate and water were added. The organic layer was separated, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After removing the solvent by evaporation under reduced pressure, 4.60 g of butyl 4-nitrophenyl carbonate was obtained as a light yellow oily matter.

Workup

  1. temperatureunder cooling on ice
  2. customThe organic layer was separated
  3. washwashed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-c9a5f1352fb34dfb8ee869cf977078d0
Source dataset
uspto-grants-2013_09
Patent number
US08536343B2

Linked notes

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