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

HRID 1915321Notes

Reaction equation

HRID 1915321 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-2e103f9e071d4b219eb0c84c7dd30f8a
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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