p-Toluenesulfonic acid → HCID 15133041, compound

HRID 1086071Notes

Reaction equation

HRID 1086071 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)(O)[CH:9]([CH3:15])[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:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[C:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15133037HCID 15133037, compound

Product 1

HCID 15133041HCID 15133041, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 3,3-bis(4-fluorophenyl)-3-hydroxy-2-methylpropionate (0.5 g, 1.6 mmol) and p-toluenesulfonic acid (0.18 g) in toluene was heated at reflux for 2.5 hours. The solution was cooled and washed with saturated sodium bicarbonate solution and water. The organic layer was dried with magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 0.5% ethyl acetate in hexane to give 0.2 g of the product as a clear oil which was crystallized from petroleum ether to give 0.15 g of the title compound; m.p. =75°-76° C.

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe solution was cooled
  3. washwashed with saturated sodium bicarbonate solution and water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica eluting with 0.5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3864f2b52e6d4278b69217b090b374fc
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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