Reaction #2348096

Reaction equation

water

p-toluenesulfonic acid monohydrate

compound ( 9 )

1-(2,3-difluoro-4-ethoxy-6-methylphenyl)-2-(4-(4-pentylcyclohexyl)cyclohexyl)ethanol

water

→

1-(2,3-difluoro-4-ethoxy-6-methylphenyl)-2-(4-(4-pentylcyclohexyl)cyclohexyl)ethene

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   OtherAfter terminating
3. 3
   Otherthe reaction
4. 4
   Extractionthe aqueous layer was extracted with toluene
5. 5
   Washwashed with saturated saline
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   Otherthe resulting residue was purified by silica gel column chromatography
9. 9
   Othersubjected to recrystallization

Procedure

0.16 g of p-toluenesulfonic acid monohydrate was added to the compound (9) having been dissolved in 60 mL of toluene, and the mixture was heated under stirring by using a Dean-Stork trap until completion of azeotrope of water. After terminating the reaction by adding water, the aqueous layer was extracted with toluene, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography and then subjected to recrystallization to obtain 11.2 g of 1-(2,3-difluoro-4-ethoxy-6-methylphenyl)-2-(4-(4-pentylcyclohexyl)cyclohexyl)ethene (Compound 1-3-3-10) as colorless crystals.

Source