Toluene → o-Nitrophenyl cyclopropyl ketone

HRID 2380081Notes

Reaction equation

HRID 2380081 reaction equation
C1(C)C=CC=CC=1.Cl[CH2:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21])=[O:13].[OH-].[Na+]>O>[CH:11]1([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[O:13])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 118064124-Chloro-2'-nitrobutyrophenone

Product 1

HCID 10487947o-Nitrophenyl cyclopropyl ketoneYield 23.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 13.8% toluene solution of 4-chloro-2'-nitrobutyrophenone obtained in Example 6 is treated, with stirring, first with 90 mL water and second with 50% NaOH (48 g, 0.6 mole NaOH). The resultant reaction mixture is allowed to exotherm, then is heated at 85°-90° C. for 2-3 hours, cooled to room temperature and allowed to settle. The phases are separated and the organic phase is washed with water. The aqueous phases are combined and washed with toluene. The organic phases are combined and concentrated in vacuo to give the title product as a toluene solution, 235 g, 23.6% title product by LC analysis (91% yield from furanone). The product solution is used as is in Example 8.

Workup

  1. customThe resultant reaction mixture
  2. temperatureis heated at 85°-90° C. for 2-3 hours
  3. customThe phases are separated
  4. washthe organic phase is washed with water
  5. washwashed with toluene
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5ce432022d24f8abe3808ece7c815d0
Source dataset
uspto-grants-1994_11
Patent number
US05364968

Reaction notes

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