Nitric Acid → Methyl 2-(4-chloro-3-nitrophenyl)-2-methylpropionate

HRID 352384Notes

Reaction equation

HRID 352384 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1>>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:16]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 22709436Methyl 2-(4-chlorophenyl)-2-methylpropanoate

Product 1

HCID 22709425Methyl 2-(4-chloro-3-nitrophenyl)-2-methylpropionateYield 100%

Procedure

After dropwise addition of 40.0 g of concentrated nitric acid to 90.7 g of concentrated sulfuric acid under ice cooling, 62.3 g of methyl 2-(4-chlorophenyl)-2-methylpropionate was added dropwise. The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure, whereby 75.5 g of the title compound was obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b500b76b8e7f44c3b311539eb0c3d430
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

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