3,4-Dimethoxybenzeneacetonitrile → HCID 9818186, compound

HRID 2222328Notes

Reaction equation

HRID 2222328 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11]COCCOC)[CH:6]=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:23][C:24]#[N:25]>>[CH3:18][O:19][C:20]1[CH:21]=[C:22](/[C:23](=[CH:6]/[C:5]2[CH:8]=[CH:9][C:10]([OH:11])=[C:3]([O:2][CH3:1])[CH:4]=2)/[C:24]#[N:25])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

3

Reactant 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 13880655HCID 13880655, compound

Product 1

HCID 9818186HCID 9818186, compoundYield 51%

Procedure

The hydroxyl group of 4-hydroxy-3-methoxybenzaldehyde (1.4 g) was protected by use of 2-methoxyethoxymethyl chloride (1.7 g) in accordance with (production process 1), to thereby produce 3-methoxy-4-methoxyethoxymethoxybenzaldehyde (0.8 g, yield: 31%). The thus-produced 3-methoxy-4-methoxyethoxymethoxybenzaldehyde (0.8 g) and 3,4-dimethoxybenzyl cyanide (0.6 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 (0.5 g, yield: 51%).

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-4dd65ff94434462fa58c33e65547086e
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

Loading…