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

HRID 73989Notes

Reaction equation

HRID 73989 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-7105f96985014f91850aa151ee6dda13
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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