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

HRID 423816Notes

Reaction equation

HRID 423816 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-6d22ccdfe9df4030b2117596bf16c74d
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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