p-Toluenesulfonic acid → HCID 58660700, compound

HRID 2115156Notes

Reaction equation

HRID 2115156 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH2:23][CH2:24][C:25]([O:27]CC)=[O:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:20]([CH:17]1[CH2:18][CH2:19][CH:14]([CH:11]2[CH2:10][CH2:9][CH:8]([C:5]3[CH:4]=[C:3]4[C:2](=[CH:7][CH:6]=3)[O:26][C:25](=[O:27])[CH2:24][CH2:23]4)[CH2:13][CH2:12]2)[CH2:15][CH2:16]1)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 58660684HCID 58660684, compound

Product 1

HCID 58660700HCID 58660700, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The foregoing ethyl 3-(2-hydroxy-5-(4-(4-propylcyclohexyl)cyclohexyl)phenyl)propionate was dissolved in toluene, to which was then added p-toluenesulfonic acid (100 mg). A Dean-Stark apparatus was attached, and the mixture was stirred under reflux by heating for 3 hours. After completion of the reaction, the reaction mixture was washed with water, rinsed with a sodium hydrogencarbonate aqueous solution, and then dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo and then subjected to isolation and purification by silica gel column chromatography, thereby obtaining a titled compound (100 mg). As a result of a variety of instrumental analyses, it was confirmed that this was the titled compound.

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 3 hours
  3. customAfter completion of the reaction
  4. washthe reaction mixture was washed with water
  5. washrinsed with a sodium hydrogencarbonate aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated in vacuo
  8. customsubjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-96a7346418f048f2895a45c2527fb7a2
Source dataset
uspto-grants-2008_10
Patent number
US07435455B2

Reaction notes

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