p-Toluenesulfonic acid → Ethyl (3,4,6-Trifluoro-2-methylbenzoyl)acetate

HRID 2394940Notes

Reaction equation

HRID 2394940 reaction equation
[CH3:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[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>[CH3:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[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 17879412Diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate

Product 1

HCID 14517129Ethyl (3,4,6-Trifluoro-2-methylbenzoyl)acetateYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.1 g) are added water (20 ml) and p-toluenesulfonic acid (30 mg) and the mixture is refluxed for 2.5 hours. After cooling, the resultant is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (3.3 g).

Workup

  1. temperaturethe mixture is refluxed for 2.5 hours
  2. temperatureAfter cooling
  3. extractionthe resultant is extracted with diethyl ether
  4. dry with materialthe extract is dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d13551e9cb944559b2f54b0694f07004
Source dataset
uspto-grants-1998_09
Patent number
US05811576

Reaction notes

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