p-Toluenesulfonic acid → HCID 57825182, compound

HRID 1668698Notes

Reaction equation

HRID 1668698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)(O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54919092HCID 54919092, compound

Product 1

HCID 57825182HCID 57825182, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(3-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol (31 g, ca. 100 mmol) in toluene (250 mL) was heated at reflux with para-toluenesulfonic acid (200 mg) in a Dean-Stark apparatus for 4 h. After TLC indicated complete conversion of starting material, the solution was left to cool, evaporated under reduced pressure and purified by flash chromatography (100 g silica gel, gradient cyclohexane 100% to 4% ethyl acetate in cyclohexane, eluant ca. 1 L, Rf 0.25 with 4% ethyl acetate in cyclohexane) to give a yellow oil (17.8 g, 62% over 2 steps).

Workup

  1. waitthe solution was left
  2. temperatureto cool
  3. customevaporated under reduced pressure
  4. custompurified by flash chromatography (100 g silica gel, gradient cyclohexane 100% to 4% ethyl acetate in cyclohexane, eluant ca. 1 L, Rf 0.25 with 4% ethyl acetate in cyclohexane)
  5. customto give a yellow oil (17.8 g, 62% over 2 steps)

Sources & evidence

ORD record
ord-aa6c785906de4d508e47622325888053
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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