p-Toluenesulfonic acid → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one

HRID 2399425Notes

Reaction equation

HRID 2399425 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][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[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>[CH:20]1([O:19][C:13]2[CH:12]=[C:11]([C:6]3([C:9]#[CH:10])[CH2:5][CH2:4][C:3](=[O:2])[CH2:8][CH2:7]3)[CH:16]=[CH:15][C:14]=2[O:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10689764HCID 10689764, compound

Product 1

HCID 108289304-(3-Cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-oneYield 97.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one dimethyl ketal (0.13 g, 0.36 mmol) and p-toluenesulfonic acid (catalytic amount) in acetone (5 mL) was stirred under an argon atmosphere at room temperature for 1.5 h. The mixture was concentrated, diluted with ethyl acetate and washed with water. The organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo to provide an oil (0.11 g, 97%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed 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-290c052eca98410fa4c4e2f63ddc8075
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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