p-Toluenesulfonic acid → 1-(2-Nitro-4-trifluoromethylphenyl)-butan-1,3-dione

HRID 342957Notes

Reaction equation

HRID 342957 reaction equation
[N+:1]([C:4]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:5]=1[C:6]([CH:8]([C:16](=[O:18])[CH3:17])C(OC(C)(C)C)=O)=[O:7])([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:5]=1[C:6](=[O:7])[CH2:8][C:16](=[O:18])[CH3:17])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54005510HCID 54005510, compound

Product 1

HCID 540146221-(2-Nitro-4-trifluoromethylphenyl)-butan-1,3-dioneYield 68.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of crude t-butyl 2-(2-nitro-4-trifluoromethylbenzoyl)-3-oxobutanoate (9.1 g) and 4-toluenesulphonic acid (0.1 g) in dry toluene (100 ml) was stirred and heated at reflux for 3 hours. The cooled mixture was extracted with aqueous sodium hydroxide solution (2M, 2×50 ml) and water (2×50 ml). The combined aqueous extracts were acidified to pH 1 and extracted with ether (3×100 ml). The combined organic layers were washed with water (50 ml), dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from petroleum spirit (bp 60°-80° C.) to give 1-(2-nitro-4-trifluoromethylphenyl)-butan-1,3-dione (4.6 g) as an off white solid mp 80°-81° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. extractionThe cooled mixture was extracted with aqueous sodium hydroxide solution (2M, 2×50 ml) and water (2×50 ml)
  4. extractionextracted with ether (3×100 ml)
  5. washThe combined organic layers were washed with water (50 ml)
  6. dry with materialdried (anhydrous sodium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was recrystallized from petroleum spirit (bp 60°-80° C.)

Sources & evidence

ORD record
ord-26a04358adfe42c899d1a6f0fa5cb046
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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