3,4-Dimethoxybenzeneacetonitrile → (z)-2-(3,4-Dimethoxy-phenyl)-3-(3-ethoxy-4-hydroxy-phenyl)-acrylonitrile

HRID 2222334Notes

Reaction equation

HRID 2222334 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12]COCCOC)[CH:7]=O)[CH3:2].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:24][C:25]#[N:26]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23](/[C:24](=[CH:7]/[C:6]2[CH:9]=[CH:10][C:11]([OH:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)/[C:25]#[N:26])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

3

Reactant 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 87761353HCID 87761353, compound

Product 1

HCID 10448983(z)-2-(3,4-Dimethoxy-phenyl)-3-(3-ethoxy-4-hydroxy-phenyl)-acrylonitrileYield 37.7%

Procedure

The hydroxyl group of 3-ethoxy-4-hydroxybenzaldehyde (2.0 g) was protected by use of 2-methoxyethoxymethyl chloride (1.5 g) in accordance with (production process 1), to thereby produce 3-ethoxy-4-methoxyethoxymethoxybenzaldehyde (2.8 g, yield: 91%). The thus-produced 3-ethoxy-4-methoxyethoxymethoxybenzaldehyde (2.8 g) and 3,4-dimethoxybenzyl cyanide (2.0 g) were subjected to condensation in accordance with process A of (production process 2), to thereby yield an MEM form of the target product. Subsequently, the protective group was removed from the MEM form in accordance with (production process 3), to thereby produce the target product (1.35 g, yield: 37%).

Workup

  1. customto thereby yield an MEM form of the target product
  2. customSubsequently, the protective group was removed from the MEM form in accordance with (production process 3)

Sources & evidence

ORD record
ord-57b98e096a814287923c6713da48c270
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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