Benzal chloride → 1-Nonene, 9-chloro-

HRID 1416987

Reaktionsgleichung

Reaktionsgleichung von HRID 1416987
[CH:1]([Cl:10])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:11][CH:12]=[CH:13][CH:14]=[CH:15]C.Cl[CH:18]([Cl:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:1]([Cl:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[CH2:18]([Cl:25])[CH2:19][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:11]=[CH:12][CH3:13].[CH2:18]([Cl:25])[CH2:19][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:11]=[CH:12][CH:13]=[CH:14][CH3:15]

Komponenten

6

Edukt 3

HCID 7411Benzal chlorideHCID 116002,4-HexadieneHCID 53771924Nonenyl chloride

Produkt 3

HCID 701021-Nonene, 9-chloro-HCID 542995618-Decen-1-yl chlorideHCID 544146658,10-Dodecadien-1-yl chloride

Versuchsvorschrift

The so-produced nonenyl chloride (112 g; 700 mmol) was added to an equimolar amount of the 2,4-hexadiene in a 100 mL round-bottomed flask equipped with a magnetic stir bar and a reflux condenser, along with 6 g of α,α-dichlorotoluene. This solution was subsurface-sparged with nitrogen for 10 minutes. The catalyst of Example 1 (1.15 g; 1.4 mmol) was added and the reaction flask was placed in an 85° C. oil bath for 15 hours. The reaction was terminated by cooling to room temperature, followed by the addition of 300 ml of hexanes and filtering three times through 75 g of silica gel. Hexanes were removed under reduced pressure and the remaining liquid was vacuum distilled through a 2 cm×30 cm packed bed column to yield 12 g of 8-nonen-1-yl chloride (Bpt1.5 36-40° C.), 46.3 g of 8-decen-1-yl chloride (Bpt1.5 56-60° C.), 15.3 g of 8,10-dodecadien-1-yl chloride (Bpt1.5 90-91 C.), and 30.4 g of 76% purity 1,16-dichloro-8-hexadecene and high boilers that remained in the distillation pot.

Aufarbeitung

  1. customThis solution was subsurface-sparged with nitrogen for 10 minutes
  2. customwas placed in an 85° C.
  3. customfor 15 hours
  4. customThe reaction was terminated
  5. additionfollowed by the addition of 300 ml of hexanes
  6. filtrationfiltering three times through 75 g of silica gel
  7. customHexanes were removed under reduced pressure
  8. distillationdistilled through a 2 cm×30 cm

Quellen und Nachweise

ORD-Eintrag
ord-337eee4613304a5ea5e9c311e21dd3d6
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05916983

Verknüpfte Notizen

Wird geladen…