Nitric Acid → HCID 18314466, compound

HRID 277392Notes

Reaction equation

HRID 277392 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:22])[C:14]([CH3:21])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:15].[N+:23]([O-])([OH:25])=[O:24]>>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N+:23]([O-:25])=[O:24])=[CH:9][C:8]=1[C:13](=[O:22])[C:14]([CH3:21])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:15]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 22664966HCID 22664966, compound

Product 1

HCID 18314466HCID 18314466, compoundYield 83%

Procedure

To concentrated sulfuric acid (15.0 ml) at 5° C. is added 2′-chloro-2-methyl-2-carboethoxypropiophenone (4.00 g, 0.01570 mol) followed by dropwise addition of concentrated nitric acid (90%, 0.740 ml, 0.0204 mol). After stirring 5 minutes, the mixture is poured onto ice and extracted with ethyl acetate. The organic layers are washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as a yellow oil (3.90 g, 83.0%) which is identified by NMR spectral analysis.

Workup

  1. additionthe mixture is poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layers are washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5339bb7ed779466baf09978476b09283
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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