Reaction #1994264

Reaction equation

1-naphthol

2,2,2-trifluoroethyl p-toluenesulfonate

potassium carbonate

dimethyl sulfoxide

→

target compound

Yield 78.7%

1-(2,2,2-trifluoroethoxy)naphthalene

Yield 78.7%

Solvents

toluene

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   TemperatureAfter cooling
3. 3
   WashIt was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution
4. 4
   ConcentrationThe organic layer was concentrated
5. 5
   Otherobtaining 36 g of oily matter
6. 6
   workup.DISTILLATIONIt was distilled in vacuum (75° C./13 Pa)

Procedure

In a nitrogen atmosphere, a suspension of 34 g of 1-naphthol, 40 g of 2,2,2-trifluoroethyl p-toluenesulfonate, 33 g of potassium carbonate, and 80 g of dimethyl sulfoxide was heated and stirred at 100° C. for 12 hours. After cooling, 100 g of water and 200 g of toluene were added to the suspension, after which an organic layer was taken out. It was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution, then 4 times with 100 g of water. The organic layer was concentrated, obtaining 36 g of oily matter. It was distilled in vacuum (75° C./13 Pa), obtaining 28 g (yield 76%) of the target compound.

Source