Nitric Acid → Cyclopropyl(3-nitrophenyl)methanone

HRID 2293685Notes

Reaction equation

HRID 2293685 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>>[CH:9]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[C:3]([N+:12]([O-:14])=[O:13])[CH:2]=2)=[O:8])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 77029Cyclopropyl phenyl ketone

Product 1

HCID 297630Cyclopropyl(3-nitrophenyl)methanone

Conditions

Temperature
-10 °C

Procedure

A 250-mL three-necked flask equipped with a thermometer and an addition funnel is charged with fuming nitric acid (90%, 130 mL) and cooled to -10° C. Cyclopropyl phenyl ketone (21 mL) is added dropwise via the addition funnel over 15 min. During the addition of the ketone, the reaction temperature is maintained between -7° and -13° C. After stirring an additional 10 min at -10° C., the reaction mixture is poured onto 1 L of crashed ice, extracted with 700 mL of toluene, washed with two portions of 5% sodium hydroxide solution and one portion of brine, dried over magnesium sulfate and concentrated to give 28.14 g of yellow oil. Recrystallization from 50 mL of methanol gives 14.62 g of the title product as white crystals.

Workup

  1. customA 250-mL three-necked flask equipped with a thermometer and an addition funnel
  2. temperaturethe reaction temperature is maintained between -7° and -13° C
  3. extractionextracted with 700 mL of toluene
  4. washwashed with two portions of 5% sodium hydroxide solution and one portion of brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37b19b9bdb4b42729a09d6d97d54fa7f
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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