p-Toluenesulfonic acid → HCID 14371389, compound

HRID 1086067Notes

Reaction equation

HRID 1086067 reaction equation
[CH:1]1([CH:7]([C:13]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:7](=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15133036HCID 15133036, compound

Product 1

HCID 14371389HCID 14371389, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-cyclohexyl-3,3-bis(4-fluorophenyl)-3-hydroxypropionate (15.0 g, 38.6 mmol) and p-toluenesulfonic acid (2.5 g) in 250 mL of toluene was heated at reflux for 2 hours. The mixture was cooled, washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 13.3 g of the title compound; m.p. =50°-55° C.

Workup

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

Sources & evidence

ORD record
ord-b3e7f13d57a540e5adc2df0b4e9c3610
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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