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

HRID 342616Notes

Reaction equation

HRID 342616 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 mixture of 45.3 g of diethyl (2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)malonate, 30 mg of p-toluenesulfonic acid, and 120 ml of water was heated under reflux for 50 minutes. After cooling, the reaction mixture was extracted with diethyl ether, and the extract was washed with brine, and then dried and concentrated to give 34.2 g of brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 50 minutes
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with diethyl ether
  5. washthe extract was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8863449dc13f40c1b1d081be03754d1b
Source dataset
uspto-grants-1999_01
Patent number
US05859026

Reaction notes

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