p-Toluenesulfonic acid → Ethyl 2-ethyl-3,3-bis(4-fluorophenyl)propenoate

HRID 1086092Notes

Reaction equation

HRID 1086092 reaction equation
[CH2:1]([CH:3]([C:9]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:3](=[C:9]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15133040Ethyl 2-ethyl-3,3-bis(4-fluorophenyl)-3-hydroxypropionate

Product 1

HCID 15133044Ethyl 2-ethyl-3,3-bis(4-fluorophenyl)propenoateYield 89.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-ethyl-3,3-bis(4-fluorophenyl)-3-hydroxypropionate (1.0 g, 3.0 mmol) and p-toluenesulfonic acid (0.2 g) in 100 mL toluene was heated at reflux for 1.25 hours. The mixture was cooled and washed with saturated sodium bicarbonate solution and water. The solution was dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from petroleum ether to give 0.85 g of the title compound; m.p. =57°-59° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.25 hours
  3. temperatureThe mixture was cooled
  4. washwashed with saturated sodium bicarbonate solution and water
  5. dry with materialThe solution was dried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-bd21f5e29e764bbf87281077f4e6ef02
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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