p-Toluenesulfonic acid → Ethyl 6-methyl-2,3,4,5-tetrafluorobenzoylacetate

HRID 2396950Notes

Reaction equation

HRID 2396950 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([CH:10](C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6]([F:21])[C:5]([F:22])=[C:4]([F:23])[C:3]=1[F:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:1][C:2]1[C:7]([C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6]([F:21])[C:5]([F:22])=[C:4]([F:23])[C:3]=1[F:24]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53783746Diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate

Product 1

HCID 14774100Ethyl 6-methyl-2,3,4,5-tetrafluorobenzoylacetateYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate (8 g) are added water (20 ml) and p-toluenesulfonic acid (80 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 6-methyl-2,3,4,5-tetrafluorobenzoylacetate (4.5 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-7c0507db4c234d23b0f4872a194c5e50
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

Loading…