Acetonitrile → 3-Hydroxy-3-(3-pentyloxyphenyl)propionitrile

HRID 74373Notes

Reaction equation

HRID 74373 reaction equation
[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5].[C:15](#[N:17])[CH3:16]>>[OH:11][CH:10]([C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:8]=1)[CH2:16][C:15]#[N:17]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 27603123-(Pentyloxy)benzaldehyde

Product 1

HCID 673170353-Hydroxy-3-(3-pentyloxyphenyl)propionitrile

Procedure

Addition of acetonitrile to 3-pentyloxybenzaldehyde gave 3-hydroxy-3-(3-pentyloxyphenyl)propionitrile as a yellow oil. Yield (1.11 g, 67%): 1H NMR (400 MHz, CDCl3) δ 7.30 (d, J=7.6 Hz, 1H), 6.92-6.98 (m, 2H), 6.87 (d, J=7.6 Hz, 1H), 5.02 (m, 1H), 3.98 (t, J=6.4 Hz, 2H), 2.76 (d, J=6.0 Hz, 2H), 1.75-1.83 (m, 2H), 1.32-1.49 (m, 4H), 0.92 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-70c783aa58b84be6a609caef2d9f929b
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

Loading…