Potassium Nitrate → 4-Tert-butyl-2-chloro-5-nitrophenyl methyl carbonate

HRID 1915317Notes

Reaction equation

HRID 1915317 reaction equation
[C:1](=[O:16])([O:14][CH3:15])[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][C:4]=1[Cl:13].[N+:17]([O-])([O-:19])=[O:18].[K+]>OS(O)(=O)=O>[C:1](=[O:16])([O:14][CH3:15])[O:2][C:3]1[CH:8]=[C:7]([N+:17]([O-:19])=[O:18])[C:6]([C:9]([CH3:11])([CH3:12])[CH3:10])=[CH:5][C:4]=1[Cl:13]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 574702304-Tert-butyl-2-chlorophenyl methyl carbonate

Product 1

HCID 574702314-Tert-butyl-2-chloro-5-nitrophenyl methyl carbonateYield 2,740.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-tert-Butyl-2-chlorophenyl methyl carbonate (36.0 g, 0.15 mol) was dissolved in conc. H2SO4 (100 mL) at 0° C. KNO3 (0.53 g, 5.2 mmol) was added in portions over 25 min. The reaction was stirred for 1.5 h and poured into ice (200 g). The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with aq. NaHCO3, dried over Na2SO4 and concentrated under vacuum to give 4-tert-butyl-2-chloro-5-nitrophenyl methyl carbonate (41.0 g), which was used without further purification.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. washThe combined organic layers were washed with aq. NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-78f85750888f415793db68f66ca386ac
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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