Reaction #2328979

Reaction equation

water

trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate

2,3-difluoro-4-ethoxyphenol

tripotassium phosphate

→

4-ethoxy-2,3-difluoro-1-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene

Yield 68.9%

Solvents

DMF

Conditions

Workup

1. 1
   Extractionextracted with toluene
2. 2
   Washwashed in turn with water, 10% hydrochloric acid, water, and saturated saline
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
5. 5
   Otherthe residue was purified in turn
6. 6
   Otherby subjecting to column chromatography (silica gel/toluene), recrystallization (methanol/acetone), column chromatography (alumina/acetone)
7. 7
   Washwashing with ion-exchange water, silica treatment, and recrystallization (methanol/acetone)

Procedure

9.8 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate and 5.96 g of 2,3-difluoro-4-ethoxyphenol were dissolved in 90 mL of DMF. 10.4 g of tripotassium phosphate was added, followed by stirring at 90 to 100° C. for 3 hours. The reaction mixture was poured into water, extracted with toluene, washed in turn with water, 10% hydrochloric acid, water, and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified in turn by subjecting to column chromatography (silica gel/toluene), recrystallization (methanol/acetone), column chromatography (alumina/acetone), washing with ion-exchange water, silica treatment, and recrystallization (methanol/acetone) to obtain 8.5 g of 4-ethoxy-2,3-difluoro-1-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene (IIIa) as a colorless crystal.

Source