Veratraldehyde → (2Z)-3-(3,4-dimethoxyphenyl)-2-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH:25]=O>>[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[CH:25]=[C:17](/[C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:16][CH:15]=2)\[C:18]#[N:19])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]Participants
3
Procedure
(2Z)-3-(3,4-dimethoxyphenyl)-2-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile is prepared starting from {4-[(8-hydroxyoctyl)oxy]phenyl}acetonitrile and commercial 3,4-dimethoxybenzaldehyde according the same procedure following for example 1 in 65% yield. This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.
Sources & evidence
- ORD record
- ord-65e88aef8a644f95996ec7d9afd6a1c4
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09366906B2
Reaction notes
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