Acetonitrile → 3-(3-(2-Methoxy-ethoxy)-phenyl)-3-hydroxypropionitrile

HRID 875545Notes

Reaction equation

HRID 875545 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[C:14](#[N:16])[CH3:15]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]([OH:10])[CH2:15][C:14]#[N:16])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 64855613-(2-Methoxyethoxy)benzaldehyde

Product 1

HCID 673162573-(3-(2-Methoxy-ethoxy)-phenyl)-3-hydroxypropionitrile

Procedure

Addition of acetonitrile to 3-(2-methoxy-ethoxy)benzaldehyde gave 3-(3-(2-methoxy-ethoxy)-phenyl)-3-hydroxypropionitrile as yellow oil. Yield (1.4 g, 63%): 1H NMR (400 MHz, CDCl3) δ 7.27-7.32 (m, 1H), 6.95-7.0 (m, 2H), 6.91 (dd, J=8.0, 1.8 Hz, 1H), 5.0 (t, J=6.2 Hz, 1H), 4.12 (t, J=4.8 Hz, 2H), 3.76 (t, J=4.8 Hz, 2H), 3.48 (s, 3H), 2.75 (d, J=6.2 Hz, 2H).

Sources & evidence

ORD record
ord-7ea91fde8f81460db1c8253eba07aac0
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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