Benzyl Alcohol → 3-(Benzyloxy)-2-methylpropanenitrile

HRID 1448653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448653
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:11](#[N:15])[C:12]([CH3:14])=[CH2:13].OS(O)(=O)=O>CCOCC>[CH2:1]([O:8][CH2:13][CH:12]([CH3:14])[C:11]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 31368Methacrylonitrile

Produkt 1

HCID 135315353-(Benzyloxy)-2-methylpropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Benzyl alcohol (108 g.; 1 mole) was stirred and treated with 0.3 g. of 50% by weight sodium hydride in a mineral oil dispersion. To the resulting solution was added dropwise 415 ml. (335 g.; 5 moles) of methacrylonitrile over a 40 minute period, at room temperature. The reaction mixture was heated at 60°-65° C. for 5 hours then cooled, acidified with 1 N aqueous H2SO4 and diluted with ether. The ether solution was washed twice with saturated brine then dried, filtered and concentrated in vacuo. Distillation of the residue gave, after removal of low boiling materials, 149.3 g. (85%) of rac. 3-benzyloxy-2-methylpropionitrile as a colorless liquid, b.p. 90°-93° C. (0.02 mm Hg.).

Aufarbeitung

  1. additiontreated with 0.3 g
  2. additionTo the resulting solution was added dropwise 415 ml
  3. customat room temperature
  4. temperatureThe reaction mixture was heated at 60°-65° C. for 5 hours
  5. temperaturethen cooled
  6. washThe ether solution was washed twice with saturated brine
  7. customthen dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. distillationDistillation of the residue
  11. customgave
  12. customafter removal of low boiling materials, 149.3 g

Quellen und Nachweise

ORD-Eintrag
ord-aa4bfdb70e1f40a9b980fa3d2604943c
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04180682

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