1-Propanol → 4-Nitrophenyl propyl carbonate

HRID 43278Notes

Reaction equation

HRID 43278 reaction equation
[CH2:1](O)[CH2:2][CH3:3].C(N(CC)CC)C.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14].C(OCC)(=[O:27])C>O1CCCC1.O>[C:13](=[O:27])([O:14][CH2:1][CH2:2][CH3:3])[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 10311-PropanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 544839324-Nitrophenyl propyl carbonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a solution of 0.75 g of propanol and 1.90 mL of triethylamine in 10 mL of tetrahydrofuran, a solution of 2.50 g of 4-nitrophenyl chloroformate in 15 mL of tetrahydrofuran was dropped under cooling on ice. After stirring at room temperature for 20 min, ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with water and a saturated sodium chloride aqueous solution successively, dried over anhydrous magnesium sulfate, followed by solvent removal by evaporation under reduced pressure. To the residue, hexane was added, and insoluble matters were removed by filtration. After removing the solvent by evaporation under reduced pressure, 2.59 g of 4-nitrophenyl propyl carbonate was obtained as a light yellow oily matter.

Workup

  1. temperatureunder cooling on ice
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated sodium chloride aqueous solution successively, dried over anhydrous magnesium sulfate
  5. customfollowed by solvent removal by evaporation under reduced pressure
  6. additionTo the residue, hexane was added
  7. custominsoluble matters were removed by filtration
  8. customAfter removing the solvent
  9. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-4a54553c28ee4c669b38fbcba0a77e1c
Source dataset
uspto-grants-2013_09
Patent number
US08536343B2

Reaction notes

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