p-Toluenesulfonic acid → HCID 15295203, compound

HRID 1780855Notes

Reaction equation

HRID 1780855 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH:22]([F:24])[F:23])[CH:12]=2)([C:9]#[CH:10])[CH2:5][CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[F:23][CH:22]([F:24])[O:21][C:13]1[CH:12]=[C:11]([C:6]2([C:9]#[CH:10])[CH2:7][CH2:8][C:3](=[O:2])[CH2:4][CH2:5]2)[CH:16]=[CH:15][C:14]=1[O:17][CH:18]([F:19])[F:20]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 56607324HCID 56607324, compound

Product 1

HCID 15295203HCID 15295203, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(3,4-bisdifluoromethoxyphenyl)-4-ethynylcyclohexan-1-one dimethyl ketal (0.2 g, 0.53 mmol) and p-toluenesulfonic acid (catalytic amount) in acetone (10 mL) was stirred under an argon atmosphere at room temperature for 0.5 h. The mixture was concentrated, was diluted with methylene chloride and was washed with water. The organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo to provide an oil (0.17 g, 98%). Analysis Calc. for C16H14F4O3 : C 58.19, H 4.27; found: C 58.30, H 4.40.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwas diluted with methylene chloride
  3. washwas washed with water
  4. extractionThe organic extract
  5. dry with materialwas dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-008cf21d007d46a0b0587455917c11a0
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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