3,4-Dimethoxybenzeneacetonitrile → HCID 10267333, compound

HRID 2222332Notes

Reaction equation

HRID 2222332 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:17])[C:9]=1[O:10]COCCOC)[CH:5]=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:5]/[C:4]2[CH:7]=[C:8]([CH3:17])[C:9]([OH:10])=[C:2]([CH3:1])[CH:3]=2)/[C:24]#[N:25])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

3

Reactant 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 23046188HCID 23046188, compound

Product 1

HCID 10267333HCID 10267333, compoundYield 57.8%

Procedure

The hydroxyl group of 3,5-dimethyl-4-hydroxybenzaldehyde (2.3 g) was protected by use of 2-methoxyethoxymethyl chloride (3.4 g) in accordance with (production process 1), to thereby produce 3,5-dimethyl-4-methoxyethoxymethoxybenzaldehyde (2.7 g, yield: 62%). The thus-produced 3,5-dimethyl-4-methoxyethoxymethoxybenzaldehyde (2.0 g) and 3,4-dimethoxybenzyl cyanide (1.5 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 (1.5 g, yield: 57%).

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-2b571cd0500d4991a4ef6110fc6bc58e
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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