p-Toluenesulfonic acid → HCID 15839203, Verbindung
Reaktionsgleichung
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:10])[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.[C-:28]#[N:29].[K+]>C1COCC1.O>[OH:24][CH:8]([C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10])[C:28]#[N:29]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
42.3 g (0.201 mol of 2,2-diphenylpropionitrile [sic] were dissolved in 230 ml of THF, and 41.4 g (0.217 mol) of p-toluenesulfonic acid were added. Then 14.09 g (0.217 mol) of KCN in 60 ml of water were added dropwise. The mixture was then heated at 40° C. for 3 hours. The reaction mixture was concentrated to about 30% under reduced pressure, taken up in water and extracted three times with ethyl acetate. The combined organic phases were washed twice with sodium disulfite solution, dried with MgSO4 and concentrated under reduced pressure. The crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1). 41.2 g (86%) of 2-hydroxy-3,3-diphenylbutyronitrile were obtained.
Aufarbeitung
- concentrationThe reaction mixture was concentrated to about 30% under reduced pressure
- extractionextracted three times with ethyl acetate
- washThe combined organic phases were washed twice with sodium disulfite solution
- dry with materialdried with MgSO4
- concentrationconcentrated under reduced pressure
- customThe crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-b87f53d694964e8fa907c0c3fecfdb4a
- Quelldatensatz
- uspto-grants-2004_02
- Patentnummer
- US06686369B1
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