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

HRID 486256

Reaction equation

HRID 486256 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-3a43c96a92d64264b8c5fdd0cb6dd558
Source dataset
uspto-grants-1994_03
Patent number
US05290934

Linked notes

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