Acetonitrile → 3-Hydroxy-3-(3-(2-hydroxy-3-methylbutoxy)phenyl)propanenitrile

HRID 1014656Notes

Reaction equation

HRID 1014656 reaction equation
[OH:1][CH:2]([CH:13]([CH3:15])[CH3:14])[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])[CH:13]([CH3:15])[CH3:14])[CH:6]=1)[CH2:17][C:16]#[N:18]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 580277143-(2-Hydroxy-3-methylbutoxy)benzaldehyde

Product 1

HCID 580277043-Hydroxy-3-(3-(2-hydroxy-3-methylbutoxy)phenyl)propanenitrile

Procedure

Addition of acetonitrile to benzaldehyde 135 following the method used in Example 34 gave 3-hydroxy-3-(3-(2-hydroxy-3-methylbutoxy)phenyl)propanenitrile (136) as a yellow oil. Yield (0.72 g, 55%): 1H NMR (400 MHz, CDCl3) δ 7.29-7.34 (m, 1H), 6.96-7.0 (m, 2H), 6.89 (dd, J=8.2, 2.0 Hz, 1H), 5.0-5.05 (m, 1H), 4.05 (dd, J=9.2, 2.8 Hz, 1H), 3.92 (dd like t, J=8.4 Hz, 1H), 3.72-3.76 (m, 1H), 2.77 (d, J=6.0 Hz, 2H), 2.44 (d, J=3.6 Hz, 1H), 2.25 (d, J=3.6 Hz, 1H), 1.84-1.93 (m, 1H), 1.04 (d, J=6.8 Hz, 3H), 1.0 (d, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-91d0c5a5902c4427a7cc0d61a8acddec
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

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