Diethyl Ether → 4-(3-Methoxyphenyl)butanenitrile

HRID 1736503Notes

Reaction equation

HRID 1736503 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14]I)[CH:9]=[CH:10][CH:11]=1.C(OCC)C>CS(C)=O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][C:1]#[N:2])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 127653893-(3-Methoxyphenyl)propyl iodide

Product 1

HCID 5789544-(3-Methoxyphenyl)butanenitrileYield 89.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A magnetically stirred suspension of sodium cyanide (13.65 g, 265 mmol) in anhydrous methyl sulfoxide (65 mL) was treated dropwise with 3-(3-methoxyphenyl)propyl iodide (66.25 g, 240 mmol) at a rate sufficient to keep the temperature below 45° C. The suspension was heated at 90° C. for 1 h, cooled to room temperature, poured over ice (1000 g), treated with diethyl ether (500 mL), the layers separated, and the aqueous portion back-extracted with diethyl ether (2×300 mL). The combined organic extracts were washed with water (3×500 mL), 6N HCl (500 mL), brine (500 mL), dried (MgSO4), filtered, and concentrated in vacuo to a clear liquid. Kugelrohr distillation (0.1 torr, 120° C.) provided the desired product as a clear liquid (37.62 g, 89%): 1H NMR (CDCl3) δ 7.25 (t, J=8 Hz, 1H), 6.78-6.69 (m, 3H), 3.80 (s, 3H), 2.75 (t, J=8 Hz, 2H), 2.31 (t, J=8 Hz, 2H), 1.98 (quint, J=8 Hz, 2H).

Workup

  1. customthe temperature below 45° C
  2. temperaturecooled to room temperature
  3. customthe layers separated
  4. extractionthe aqueous portion back-extracted with diethyl ether (2×300 mL)
  5. washThe combined organic extracts were washed with water (3×500 mL), 6N HCl (500 mL), brine (500 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a clear liquid
  9. distillationKugelrohr distillation (0.1 torr, 120° C.)

Sources & evidence

ORD record
ord-ff87bbf2bebd45bba64e2347e0369705
Source dataset
uspto-grants-1996_07
Patent number
US05541228

Reaction notes

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