Nitric Acid → 4-Chloro-3-nitrophenyl cyclopropyl ketone

HRID 2402348Notes

Reaction equation

HRID 2402348 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]2[CH2:11][CH2:12]2)=[O:9])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 811484-Chlorophenyl cyclopropyl ketone

Product 1

HCID 12682594-Chloro-3-nitrophenyl cyclopropyl ketone

Conditions

Temperature
5 °C

Procedure

Under argon and at −10° C., 20 g (110.7 mmol) of (4-chlorophenyl)(cyclopropyl)methanone were added slowly to 60 ml of concentrated nitric acid. The reaction mixture was then slowly warmed to 5° C. and stirred at this temperature for 6 h. Carefully, the reaction solution was then added with stirring to about 100 ml of ice-water. This resulted in the precipitation of a white solid which was filtered off with suction and washed repeatedly with water. The solid obtained in this manner was then dried under high vacuum. This gave 24.3 g (97% of theory) of the desired product.

Workup

  1. additionCarefully, the reaction solution was then added
  2. customThis resulted in the precipitation of a white solid which
  3. filtrationwas filtered off with suction
  4. washwashed repeatedly with water
  5. customThe solid obtained in this manner
  6. customwas then dried under high vacuum

Sources & evidence

ORD record
ord-aff21bc8cc554f5f945f66d09358ccf5
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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