Sodium Hydroxide → o-Nitrophenyl cyclopropyl ketone

HRID 2380077Notes

Reaction equation

HRID 2380077 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])=[O:6].[OH-].[Na+]>O.C(OCC)C>[CH:4]1([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 537739744-Bromo-2'-nitrobutyrophenone

Product 1

HCID 10487947o-Nitrophenyl cyclopropyl ketone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 4-bromo-2'-nitrobutyrophenone (3.44 g, 0.013 mole) and NaOH (0.76 g, 0.019 mole) in water is heated at reflux temperature until reaction is complete by TLC, cooled to room temperature and extracted with diethyl ether. The ether extracts are combined, dried over Na2SO4 and concentrated in vacuo to give a dark brown liquid residue. The residue is taken up in diethyl ether, filtered through silica gel and concentrated in vacuo to give the title product as a yellow oil, identified by 1HNMR.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature
  3. customuntil reaction
  4. extractionextracted with diethyl ether
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a dark brown liquid residue
  8. filtrationfiltered through silica gel
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0809fa1c0dc04d5da83ccd3896d794dd
Source dataset
uspto-grants-1994_11
Patent number
US05364968

Reaction notes

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