Water → 4-(Benzyloxy)cyclohexane-1-carbonitrile

HRID 587123Notes

Reaction equation

HRID 587123 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([NH2:17])=O)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]#[N:17])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 71239712HCID 71239712, compound

Product 1

HCID 467807704-(Benzyloxy)cyclohexane-1-carbonitrileYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(benzyloxy)cyclohexanecarboxamide (2.33 g, 10 mmol, 1.0 equiv) in THF (dry, 50 mL) was added trifluoroacetic anhydride (4.16 mL, 30 mmol, 3.0 equiv) dropwise at room temperature. The resulting clear solution was stirred at room temperature for 30 min and then concentrated to give the residue. H2O (50 mL) was added. The aqueous phase was extracted with MTBE (3×50 mL). The combined organic solution was washed with brine (50 mL), dried over anhydrous Na2SO4, concentrated to give 2.1 g (yield 97%) of 4-(benzyloxy)cyclohexanecarbonitrile as a pale yellow oil.

Workup

  1. concentrationconcentrated
  2. customto give the residue
  3. extractionThe aqueous phase was extracted with MTBE (3×50 mL)
  4. washThe combined organic solution was washed with brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e14e4a929f846929471cfb5ccb6d7da
Source dataset
uspto-grants-2016_01
Patent number
US09226923B2

Reaction notes

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