p-Toluenesulfonic acid → Ethyl 2-[bis(4-fluorophenyl)methylidene]-3-methylbutanoate

HRID 1086062Notes

Reaction equation

HRID 1086062 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)(O)[CH:9]([CH:15]([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:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:9]([CH:15]([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 14033523HCID 14033523, compound

Product 1

HCID 14033524Ethyl 2-[bis(4-fluorophenyl)methylidene]-3-methylbutanoateYield 45.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3,3-bis(4-fluorophenyl)-3-hydroxy-2-(1-methylethyl)propionate (0.35 g, 1 mmol) and p-toluene sulfonic acid (0.1 g) in 20 mL toluene was heated at reflux for 1.5 hours. The mixture was concentrated in vacuo and the residue dissolved in diethyl ether. The ether solution was washed with saturated sodium bicarbonate solution, dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from cold petroleum ether to give 0.15 g of the title compound; m.p. =51.5°-52.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in diethyl ether
  5. washThe ether solution was washed with saturated sodium bicarbonate solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from cold petroleum ether

Sources & evidence

ORD record
ord-5e5499ce6078447195186bc14653b7e5
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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