Acetic Acid → 3-Cyano-3-methylbutyltrimethoxysilane

HRID 1707790Notes

Reaction equation

HRID 1707790 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[CH3:3].[Na].[CH:7]([Si:9]([O:14][CH3:15])([O:12][CH3:13])[O:10][CH3:11])=[CH2:8].C(O)(=O)C>>[C:1]([C:2]([CH3:4])([CH3:3])[CH2:8][CH2:7][Si:9]([O:14][CH3:15])([O:12][CH3:13])[O:10][CH3:11])#[N:5]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6559IsobutyronitrileHCID 76004VinyltrimethoxysilaneHCID 5360545Sodium

Product 1

HCID 189626083-Cyano-3-methylbutyltrimethoxysilaneYield 73%

Conditions

Temperature
103 °C

Procedure

Under a nitrogen atmosphere, isobutyronitrile (297.4 grams, 4.3 moles) and sodium metal spheres (9.9 grams, 0.43 moles) were added to a flask as described in Example 6. The contents of the flask were heated to 103° C with stirring and vinyltrimethoxysilane (637.8 grams, 4.3 moles) was added. After removing the heat source, the temperature of the flask contents was maintained at 100° C. to 107° C. by the rate of addition of the vinyltrimethoxysilane. After adding all of the vinyltrimethoxysilane, the flask contents were heated to 150° C. for one hour to ensure complete reaction. A sample taken for infra-red analysis showed no signs of any absorption attributable to a vinyl group on silicon. The infra-red spectrum was entirely consistent with the proposed structure and indicated a high state of purity. After cooling to room temperature, 25.8 grams (0.43 moles) of glacial acetic acid was added to neutralize any residual basic material. The reaction product was filtered and vacuum distilled (boiling point, 76° C. to 77° C. at 0.3 mm Hg) to yield 681.4 grams (73% yield after distillation) of 3-cyano-3-methylbutyltrimethoxysilane, as characterized by 1H and 13C NMR spectroscopy.

Workup

  1. additionwere added to a flask
  2. customAfter removing the heat source
  3. temperaturethe temperature of the flask contents was maintained at 100° C. to 107° C. by the rate of addition of the vinyltrimethoxysilane
  4. additionAfter adding all of the vinyltrimethoxysilane
  5. temperaturethe flask contents were heated to 150° C. for one hour
  6. customreaction
  7. customno signs of any absorption attributable to a vinyl group on silicon
  8. temperatureAfter cooling to room temperature
  9. filtrationThe reaction product was filtered
  10. distillationvacuum distilled (boiling point, 76° C. to 77° C. at 0.3 mm Hg)

Sources & evidence

ORD record
ord-98ed8be9259741f1895341bbd10ccc9a
Source dataset
uspto-grants-1994_10
Patent number
US05354880

Reaction notes

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