Sodium Cyanide → 1-Hydroxy-4-trifluoroethoxycyclohexanecarbonitrile

HRID 2088281Notes

Reaction equation

HRID 2088281 reaction equation
[C-:1]#[N:2].[Na+].[F:4][C:5]([F:16])([F:15])[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>O>[OH:14][C:11]1([C:1]#[N:2])[CH2:10][CH2:9][CH:8]([O:7][CH2:6][C:5]([F:15])([F:16])[F:4])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 24346Disodium disulfiteHCID 595627824-(2,2,2-Trifluoroethoxy)cyclohexanone

Product 1

HCID 595627671-Hydroxy-4-trifluoroethoxycyclohexanecarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

13.74 g of sodium cyanide are dissolved in 200 ml of water. Over a period of 30 min, 50 g of 4-trifluoroethoxycyclohexanone are then added dropwise at 20-28° C. with slight cooling. The mixture is stirred at 25° C. for 5 minutes, and 31.48 g of sodium disulfite, dissolved in 100 ml of water, are then added dropwise with cooling at 25-30° C. over a period of 30 min. With monitoring by thin-layer chromatography, the mixture is stirred at room temperature. The aqueous phase is extracted 3× with in each case 90 ml of toluene. The organic phases are combined and concentrated under reduced pressure.

Workup

  1. additionare then added dropwise
  2. temperaturewith cooling at 25-30° C. over a period of 30 min
  3. stirringthe mixture is stirred at room temperature
  4. extractionThe aqueous phase is extracted 3× with in each case 90 ml of toluene
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-490d49d633c0425fa1afcfc8710ff1e0
Source dataset
uspto-grants-2013_05
Patent number
US08435549B2

Reaction notes

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