Acrylonitrile → 3-(2-Oxo-1-phenylcyclohexyl)propanenitrile

HRID 71226Notes

Reaction equation

HRID 71226 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](#[N:17])[CH:15]=[CH2:16]>O1CCOCC1>[O:13]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]1([CH2:16][CH2:15][C:14]#[N:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 955922-Phenylcyclohexanone

Product 1

HCID 2633833-(2-Oxo-1-phenylcyclohexyl)propanenitrileYield 77.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Triton B surfactant (500 μL) was added to a stirred solution of 2-phenylcyclohexanone (5 g, 28.7 mmol) in dioxane (40 mL). A solution of acrylonitrile (1.8 g, 33.9 mmol) in dioxane (5 mL) was added dropwise. A slight exotherm was observed. The solution was stirred at room temperature for 3 h and concentrated. The residue was diluted with EtOAc (50 mL) and washed with water (20 mL, 2×). The EtOAc extract was dried (MgSO4), filtered, and concentrated. The residual oil was chromatographed on a silica gel column. Elution with 2% EtOAc in heptane, followed by 5% EtOAc in heptane afforded 3-(2-oxo-1-phenylcyclohexyl)propanenitrile (5.05 g, 77% yield) as a colorless oil. HPLC: tR=2.73 min, YMC Combi S5 ODS 4.6×50 mm, 4 min gradient, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH—0.2% H3PO4; Final solvent: 90% aq. MeOH—0.2% H3PO4. LC/MS: m/e 228.26 (M+H)+, 250.14 (M+Na)+.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (50 mL)
  3. washwashed with water (20 mL, 2×)
  4. extractionThe EtOAc extract
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual oil was chromatographed on a silica gel column
  9. washElution with 2% EtOAc in heptane

Sources & evidence

ORD record
ord-3736b13c71b94907a71b3d1057a76994
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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