Water → HCID 54160113, compound

HRID 2256901Notes

Reaction equation

HRID 2256901 reaction equation
[N+:1]([C:4]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:5]=1[C:6]([CH:8](C(=O)C)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])=[O:7])([O-:3])=[O:2].S(=O)(=O)(O)O.O>C(O)C>[N+:1]([C:4]1[CH:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][C:5]=1[C:6](=[O:7])[CH2:8][C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 54543003HCID 54543003, compound

Product 1

HCID 54160113HCID 54160113, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 2-(2-nitro4-trifluoromethylbenzoyl)-1-phenylbutan-1,3-dione (28.5 g) in ethanol (300 ml) was added to a mixture of concentrated sulphuric acid (225 ml) and ethanol (225 ml). The resultant solution was stirred and heated at 100° C. for 1 hour. The cooled solution was poured onto a mixture of ice and water (21) and extracted with dichloromethane (3×250 ml). The combined organic layers were washed with water (2×100 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-nitro4-trifluoromethylphenyl)-3-phenylpropan-1,3-dione (19.6 g) as an off-white solid mp 101°-103° C.

Workup

  1. extractionextracted with dichloromethane (3×250 ml)
  2. washThe combined organic layers were washed with water (2×100 ml)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was recrystallized from petroleum spirit (bp 60°-80° C.)

Sources & evidence

ORD record
ord-29f246b872824f9d9c6e08fad596ab66
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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