Potassium Nitrate → 2-Admantyl-4-methyl-5-nitrophenyl ethyl carbonate

HRID 2189611Notes

Reaction equation

HRID 2189611 reaction equation
[C:1](=[O:23])([O:20][CH2:21][CH3:22])[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]1[CH:17]2[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:19][CH:11]1[CH2:12]3)[CH2:16]2.[N+:24]([O-])([O-:26])=[O:25].[K+]>OS(O)(=O)=O>[C:1](=[O:23])([O:20][CH2:21][CH3:22])[O:2][C:3]1[CH:8]=[C:7]([N+:24]([O-:26])=[O:25])[C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]1[CH:11]2[CH2:19][CH:15]3[CH2:14][CH:13]([CH2:18][CH:17]1[CH2:16]3)[CH2:12]2

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 666859302-Admantyl-4-methyl-phenyl ethyl carbonate

Product 1

HCID 666862102-Admantyl-4-methyl-5-nitrophenyl ethyl carbonateYield 25%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cooled solution of 2-admantyl-4-methyl-phenyl ethyl carbonate (1.32 g, 4.2 mmol) in H2SO4 (98%, 10 mL) was added KNO3 (510 mg, 5.0 mmol) in small portions at 0° C. The mixture was stirred for 3 h while warming to room temperature, poured into ice and then extracted with dichloromethane. The combined organic layers were washed with NaHCO3 and brine, dried over MgSO4 and concentrated to dryness. The residue was purified by column chromatography (0-10% EtOAc-Hexane) to yield 2-admantyl-4-methyl-5-nitrophenyl ethyl carbonate (378 mg, 25%).

Workup

  1. additionpoured into ice
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography (0-10% EtOAc-Hexane)

Sources & evidence

ORD record
ord-6cb5ab11dbef4247b5c4c2e6af38d3ce
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

Loading…