Hydrochloric Acid → 3-(2-Methylpropenyl)benzonitrile

HRID 249138

Reaktionsgleichung

Reaktionsgleichung von HRID 249138
[I-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C.[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].[C:30]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)C=O)#[N:31].Cl>O1CCCC1.C(OCC)(=O)C>[CH3:24][C:25]([CH3:28])=[CH:26][C:38]1[CH:39]=[C:32]([CH:33]=[CH:34][CH:37]=1)[C:30]#[N:31]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 90670m-FormylbenzonitrileHCID 2723783Isopropyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 190247923-(2-Methylpropenyl)benzonitrileAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of isopropyltriphenylphosphonium iodide (24.7 g) in tetrahydrofuran (100 ml) was added a solution of potassium tert-butoxide (7.71 g) in tetrahydrofuran (50 ml) at 25° C. over 20 minutes, and the mixture was stirred for 30 minutes at the same temperature. A solution of 3-cyanobenzaldehyde (5.0 g) in tetrahydrofuran (50 ml) was added at 0° C. over 20 minutes, and the mixture was stirred at 25° C. for 1 hour. The mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The residue was chromatographed on silica gel (200 g) eluting with 10% ethyl acetate in hexane to give 3-(2-methyl-1-propenyl)benzonitrile (4.21 g) as a pale yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at 25° C. for 1 hour
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was chromatographed on silica gel (200 g)
  6. washeluting with 10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-789071311abe4400a1029af3794ba1b8
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212320

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