Water → HCID 68542744, compound

HRID 2241834Notes

Reaction equation

HRID 2241834 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.F[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=1.C(=O)([O-])[O-:22].[K+].[K+].O>CN(C)C=O>[OH:22][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[O:7][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9246Cyclohexene oxideHCID 11430Potassium CarbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 68542744HCID 68542744, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclohexene oxide (13.11 g, 133.6 mmol), 4-fluoro-2-(trifluoromethyl)benzonitrile (5.00 g, 26.72 mmol), and potassium carbonate (5.539 g, 40.08 mmol) in DMF (dimethylformamide) (50 mL) were heated to 95° C. for 14 hours. The reaction was then allowed to cool. The reaction was added to water (300 mL) and then extracted with ethyl acetate (200 mL) three times. The combined extracts were washed with water (300 mL), 0.5M NaOH (300 mL), water (300 mL), and a 15% sodium chloride solution (300 mL). The organic phase was dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on silica, eluting with a 2:1 solution of hexane:ethyl acetate. This yielded the desired product, 4-(2-hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile (3.8 g, 50% yield).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (200 mL) three times
  3. washThe combined extracts were washed with water (300 mL), 0.5M NaOH (300 mL), water (300 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by chromatography on silica
  8. washeluting with a 2:1 solution of hexane

Sources & evidence

ORD record
ord-64610008956a4222b4038278b0e0ce58
Source dataset
uspto-grants-2010_03
Patent number
US07670613B2

Reaction notes

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