Acetonitrile → 3-(3-(2,6-Dichlorobenzyloxy)phenyl]-3-hydroxypropionitrile

HRID 875553Notes

Reaction equation

HRID 875553 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[C:19](#[N:21])[CH3:20]>>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]([OH:10])[CH2:20][C:19]#[N:21])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 7354843-[(2,6-Dichlorobenzyl)oxy]benzaldehyde

Product 1

HCID 673166933-(3-(2,6-Dichlorobenzyloxy)phenyl]-3-hydroxypropionitrile

Procedure

Addition of acetonitrile to 3-(2,6-Dichlorobenzyloxy)benzaldehyde gave 3-[3-(2,6-dichlorobenzyloxy)phenyl]-3-hydroxypropionitrile as a yellow oil. Yield (1.65 g, 68%): 1H NMR (400 MHz, CDCl3) δ 7.34-7.39 (m, 3H), 7.24-7.28 (m, 1H), 7.07 (s, 1H), 7.00-7.05 (m, 2H), 5.29 (s, 2H), 5.04 (t, J=6.4 Hz, 1H), 2.78 (d, J=6.4 Hz, 2H).

Sources & evidence

ORD record
ord-a86b656d19114398a4c8b8a72d028bbd
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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