Acetonitrile → 3-Hydroxy-3-(3-(2-hydroxypentyloxy)phenyl)propanenitrile

HRID 875590Notes

Reaction equation

HRID 875590 reaction equation
[OH:1][CH:2]([CH2:13][CH2:14][CH3:15])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].[C:16](#[N:18])[CH3:17]>>[OH:9][CH:8]([C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:13][CH2:14][CH3:15])[CH:6]=1)[CH2:17][C:16]#[N:18]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 866376233-(2-Hydroxypentyloxy)benzaldehyde

Product 1

HCID 673176483-Hydroxy-3-(3-(2-hydroxypentyloxy)phenyl)propanenitrile

Procedure

Addition of acetonitrile to 3-(2-hydroxypentyloxy)benzaldehyde gave 3-hydroxy-3-(3-(2-hydroxypentyloxy)phenyl)propanenitrile as a yellow oil. Yield (0.25 g, 12%): 1H NMR (400 MHz, CDCl3) δ 7.27-7.34 (m, 1H), 6.94-7.00 (m, 2H), 6.88 (dd, J=8.0, 2.0 Hz, 1H), 5.01 (t, J=5.6 Hz, 1H), 3.96-4.06 (m, 2H), 3.83 (dd, J=8.8, 7.6 Hz, 1H), 2.76 (d, J=6.0 Hz, 2H), 1.52-1.60 (m, 2H), 1.40-1.49 (m, 2H), 0.97 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-da50b6bf3ae0400489eb4a5c6cd1d43c
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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