Butyl Chloride → 2-(2-Phenoxyphenyl)hexanenitrile

HRID 128222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 128222
[C-:1]#[N:2].[Na+].[O:4]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:19](Cl)[CH2:20][CH2:21][CH3:22].[OH-].[Na+]>O.CS(C)=O>[O:4]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]([CH2:19][CH2:20][CH2:21][CH3:22])[C:1]#[N:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 8005Butyl ChlorideHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 169302Benzene, (chloromethyl)phenoxy-

Produkt 1

HCID 197756142-(2-Phenoxyphenyl)hexanenitrileAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Into a three-necked 300 ml round-bottom flask are charged 7.4 g (0.15 mole) of sodium cyanide and 80 ml of dimethyl sulfoxide. To this slurry is added 30 g (0.13 mole) of 2-phenoxybenzyl chloride dropwise. Reaction temperature increases from 24° to 44° C. The reaction mixture is stirred for an additional 11/2 hours. To this reaction mixture is added 13.7 g (0.13 mole) of butyl chloride followed by dropwise addition of 34 g (0.4 mole) of 50% sodium hydroxide solution. After stirring for an additional 1/2 hour, reaction mixture is poured into 150 ml of water and extracted with hexane. The combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 32 g of crude product. Material can be further purified by vacuum distillation (bp 149-60/0.25 mm).

Aufarbeitung

  1. customReaction temperature
  2. temperatureincreases from 24° to 44° C
  3. stirringAfter stirring for an additional 1/2 hour
  4. customreaction mixture
  5. extractionextracted with hexane
  6. washThe combined hexane extracts are washed with water
  7. dry with materialdried over MgSO4
  8. customSolvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-992cbbc8a9db43cab0509ab776a9b49f
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259339

Notizen zur Reaktion

Wird geladen…