Water → 4-Nitrophenyl isopropyl carbonate

HRID 43279

Reaction equation

HRID 43279 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11](N(CC)CC)C.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])C.O>O1CCCC1.ClC(OC(C)C)=O>[C:18](=[O:20])([O:21][CH:22]([CH3:23])[CH3:11])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 233903734-Nitrophenyl isopropyl carbonate

Reagents, catalysts & solvents 2

HCID 7917Isopropyl chloroformateSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 3.00 g of 4-nitrophenol and 3.31 mL of triethylamine in 30 mL of tetrahydrofuran, 2.46 mL of isopropyl 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, dried over anhydrous magnesium sulfate, followed by solvent removal by evaporation under reduced pressure. The residue was dissolved in 50 mL of ethyl acetate, washed with a 5% potassium carbonate aqueous solution and a saturated sodium chloride aqueous solution successively and dried over anhydrous magnesium sulfate. After removing the solvent by evaporation under reduced pressure, 3.00 g of 4-nitrophenyl isopropyl carbonate was obtained as a light yellow solid.

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. customfollowed by solvent removal by evaporation under reduced pressure
  6. dissolutionThe residue was dissolved in 50 mL of ethyl acetate
  7. washwashed with a 5% potassium carbonate aqueous solution
  8. dry with materiala saturated sodium chloride aqueous solution successively and dried over anhydrous magnesium sulfate
  9. customAfter removing the solvent
  10. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-cc3e370ad82d4fa1bf0fa21ad081678d
Source dataset
uspto-grants-2013_09
Patent number
US08536343B2

Linked notes

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