p-Toluenesulfonic acid → HCID 15133043, compound

HRID 1086079Notes

Reaction equation

HRID 1086079 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(O)[CH:9]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:9]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15133039HCID 15133039, compound

Product 1

HCID 15133043HCID 15133043, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3,3-bis(4-fluorophenyl)-3-hydroxy-2-(1,1-dimethylethyl)propionate (1.0 g, 2.8 mmol) and p-toluenesulfonic acid (0.3 g) in 20 mL toluene was heated at reflux for 45 minutes. The mixture was cooled and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 1% ethyl acetate in hexane. Concentration of the appropriate fractions gave an oil which was crystallized from petroleum ether to give 0.35 g of the title compound; m.p. =60°-62° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 minutes
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica eluting with 1% ethyl acetate in hexane
  6. customConcentration of the appropriate fractions gave an oil which
  7. customwas crystallized from petroleum ether

Sources & evidence

ORD record
ord-619436054a6d4aa5a60df06078101291
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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