4-Nitrophenol → 4-Nitrophenyl Propionyloxymethyl Carbonate

HRID 1609748Notes

Reaction equation

HRID 1609748 reaction equation
CN1CCOCC1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O-:10])=[O:9].[C:18](Cl)(=[O:26])[O:19][CH2:20][O:21][C:22](=[O:25])[CH2:23][CH3:24]>C(Cl)Cl>[C:18](=[O:26])([O:19][CH2:20][O:21][C:22](=[O:25])[CH2:23][CH3:24])[O:17][C:14]1[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 79724-MethylmorpholineHCID 14800977Propanoyloxymethyl Carbonochloridate

Product 1

HCID 148009964-Nitrophenyl Propionyloxymethyl CarbonateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methylmorpholine (0.67 mL, 6.0 mmol) is added to a suspension of 4-nitrophenol (0.83 g, 6.0 mmol) in CH2Cl2 (10 mL) with stirring. A solution of 7c (1.27 g, 95% purity, 7.2 mmol) in CH2Cl2 (3 mL) is added during 20 min followed by stirring at 0° C. (30 min) and overnight at room temperature. After filtration the filtrate is evaporated and the residue partitioned between ice-cold Et2O (25 mL) and H2O (25 mL). The organic phase is extracted with ice-cold 0.5N NaOH (10 mL), H2O (3×15 mL), dried (MgSO4) and evaporated. The residue (1.50 g) is extracted with hexane (2×10 mL) to leave the title compound (0.98 g, 61%), mp 35°-36° C.

Workup

  1. stirringby stirring at 0° C. (30 min) and overnight at room temperature
  2. filtrationAfter filtration the filtrate
  3. customis evaporated
  4. customthe residue partitioned between ice-cold Et2O (25 mL) and H2O (25 mL)
  5. extractionThe organic phase is extracted with ice-cold 0.5N NaOH (10 mL), H2O (3×15 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. extractionThe residue (1.50 g) is extracted with hexane (2×10 mL)

Sources & evidence

ORD record
ord-72c68bd9a671449a841db7f86b3fb0f7
Source dataset
uspto-grants-1995_03
Patent number
US05401868

Reaction notes

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