p-Toluenesulfonic acid → Ethyl (2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)acetate

HRID 1078265Notes

Reaction equation

HRID 1078265 reaction equation
[F:1][C:2]1[C:20]([CH3:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([N+:24]([O-:26])=[O:25])[C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[F:1][C:2]1[C:20]([CH3:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([N+:24]([O-:26])=[O:25])[C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11793970Diethyl (2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)malonate

Product 1

HCID 10590663Ethyl (2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)acetateYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 45.3 g of diethyl (2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)malonate and 30 mg of p-toluenesulfonic acid in 120 ml of water was heated at reflux for 50 minutes. After cooling, the reaction mixture was extracted with diethyl ether. The combined organic extracts were washed with brine, dried and evaporated to give 34.2 g of the desired compound as brown oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 50 minutes
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with diethyl ether
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-5eb8e74a998c49aa973b54735318eb10
Source dataset
uspto-grants-1996_08
Patent number
US05547962

Reaction notes

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