Benzenepropanal → 2-Hydroxy-4-phenylbutanenitrile

HRID 389072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389072
[C:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC(CC(C)C)[C:13]#[N:14].OS([O-])=O.[Na+].[C-]#N.[Na+]>O>[OH:10][CH:9]([CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:13]#[N:14]

Komponenten

6

Edukt 4

HCID 7707Benzenepropanal2×HCID 8929Sodium CyanideHCID 125486402-Hydroxy-4-methylpentanenitrileHCID 23665763Sodium Bisulfite

Produkt 1

HCID 109098692-Hydroxy-4-phenylbutanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-Hydroxy-4-phenylbutanenitrile is prepared from 3-phenylpropionaldehyde according to the protocol described for 2-Hydroxy-4-methylpentanenitrile; (11.14 g, 83.2 mmol) 3-phenylpropionaldehyde, NaHSO3 (17.7 ml of solution at 37%, 83 mmol), (4.08 g, 83.2 mmol) of NaCN in H2O (18 ml). The product, a yellow oil, is used with no other purification (12.4 g, 93%); 1H NMR (100 MHz, CDCl3) δ: 2.02-2.25 (m, 2H), 2.76-2.91 (m, 2H), 3.98 (s, 1H), 4.39 (t, J=8 Hz, 1H), 7.26 (d, J=3 Hz, 5H); 13C NMR (25 MHz, CDCl3) δ: 30.49, 36.37, 59.92, 120.04, 126.28, 128.28, 128.49, 139.60. Analysis calculated for C10H11NO: C, 74.51; H, 6.88; N, 8.69. Experimental: C, 74.38; H, 6.97; N, 8.42.

Aufarbeitung

  1. customThe product, a yellow oil, is used with no other purification (12.4 g, 93%)

Quellen und Nachweise

ORD-Eintrag
ord-41f06a03c6f04233a218af68dc85ac3d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378098B2

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