Acrylonitrile → 3-(Decyloxy)propionitrile

HRID 1602473Notes

Reaction equation

HRID 1602473 reaction equation
[H-].[Na+].[CH2:3]([OH:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14](#[N:17])[CH:15]=[CH2:16]>C(OCC)C>[CH2:3]([O:13][CH2:16][CH2:15][C:14]#[N:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 81741-DecanolHCID 24758Sodium hydride

Product 1

HCID 855773-(Decyloxy)propionitrileYield 41.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (200 mg, 5 mmol; washed three times with hexane) was treated with 1-decanol (12 mL, 63 mmol) for 1 hour at room temperature. Acrylonitrile (10 mL, 152 mmol) was added dropwise and the resulting paste warmed to 60° C. for 2 hours. After cooling to room temperature, the paste was dissolved in diethyl ether and washed with copious water, one portion of brine, dried over magnesium sulfate, filtered and concentrated. Chromatography of the crude residue on silica gel using 25-75 ethyl acetate-hexane as eluant gave the title compound (5.5 g) as a water-white liquid. The structure was supported by NMR, infrared spectroscopy, elemental analysis and mass spectroscopy. Analysis for C13H25NO (MW 211.4): Calcd.: C, 73.88; H, 11.92; N, 6.63. Found: C, 74.00; H, 11.84; N, 6.49.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with copious water, one portion of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8a9dd1f6cd849db986b0c869bd99fff
Source dataset
uspto-grants-1999_11
Patent number
US05981580

Reaction notes

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