Acetonitrile → 3-(3-(4-Benzyloxy-butoxy)-phenyl]-3-hydroxypropionitrile

HRID 74387Notes

Reaction equation

HRID 74387 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](#[N:24])[CH3:23]>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:17]([OH:18])[CH2:23][C:22]#[N:24])[CH:19]=[CH:20][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 580277083-(4-Benzyloxybutoxy)benzaldehyde

Product 1

HCID 580276033-(3-(4-Benzyloxy-butoxy)-phenyl]-3-hydroxypropionitrile

Procedure

Addition of acetonitrile to 3-(4-benzyloxybutoxy)benzaldehyde gave 3-[3-(4-benzyloxy-butoxy)-phenyl]-3-hydroxypropionitrile as yellow oil. Yield (0.3 g, 52%): 1H NMR (400 MHz, CDCl3) δ 7.33-7.37 (m, 4H), 7.27-7.32 (m, 2H), 6.93-6.96 (m, 2H), 6.86 (d, J=8.0 Hz, 1H), 5.0 (t, J=6.4 Hz, 2H), 4.52 (s, 2H), 4.01 (t, J=6.2 Hz, 2H), 3.55 (t, J=6.0 Hz, 2H), 2.75 (d, J=6.4 Hz, 2H), 1.87-1.94 (m, 2H), 1.77-1.85 (m, 2H).

Sources & evidence

ORD record
ord-061dd57a2a0840a5a645aa752e2bacd7
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

Loading…