Nitric Acid → 4-Chloro-3-nitro-valerophenone

HRID 67140Notes

Reaction equation

HRID 67140 reaction equation
[Cl:1][CH:2]([CH3:13])[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[Cl:1][CH:2]([CH3:13])[CH:3]([N+:14]([O-:16])=[O:15])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 144729704-Chlorovalerophenone

Product 1

HCID 205284754-Chloro-3-nitro-valerophenone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

50 ml of concentrated sulphuric acid are treated, while stirring, with 9.9 g of 4-chloro-valerophenone, while cooling with an ice/sodium chloride mixture. The bulk of the product dissolves, a slightly exothermic reaction taking place, and a yellow suspension forms, which is treated, while stirring vigorously and at a temperature of -10° to -5°, with a mixture of 20 ml of concentrated sulphuric acid and 10.4 ml of concentrated nitric acid (d=1.52), in the course of 10 minutes. After a reaction time of five minutes, the mixture is poured onto ice and the aqueous mixture is extracted with chloroform. The organic extract is washed once with an aqueous solution of sodium carbonate and with water, dried over sodium sulphate and filtered through silica gel. 4-Chloro-3-nitro-valerophenone is obtained as an oily residue after evaporating the filtrate.

Workup

  1. dissolutionThe bulk of the product dissolves
  2. customa slightly exothermic reaction
  3. additiona yellow suspension forms, which is treated
  4. additionAfter a reaction time of five minutes, the mixture is poured onto ice
  5. extractionthe aqueous mixture is extracted with chloroform
  6. extractionThe organic extract
  7. washis washed once with an aqueous solution of sodium carbonate and with water
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-25bcc97ed35c4a8e984125c10b2a9294
Source dataset
uspto-grants-1982_08
Patent number
US04344957

Reaction notes

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