Dimethyl Sulfoxide → 1-(2,2,2-Trifluoroethoxy)naphthalene

HRID 1907082Notes

Reaction equation

HRID 1907082 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C1(C)C=CC=CC=1.O>[F:24][C:23]([F:26])([F:25])[CH2:22][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 134430561-(2,2,2-Trifluoroethoxy)naphthaleneYield 78.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

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.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. washIt was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution
  4. concentrationThe organic layer was concentrated
  5. customobtaining 36 g of oily matter
  6. distillationIt was distilled in vacuum (75° C./13 Pa)

Sources & evidence

ORD record
ord-93e74103d8e14c959f9aa4f15c4c45c2
Source dataset
uspto-grants-2013_12
Patent number
US08597869B2

Reaction notes

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