3,4-Dimethoxybenzeneacetonitrile → HCID 5896118, compound

HRID 2222330Notes

Reaction equation

HRID 2222330 reaction equation
COCCOC[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16]COCCOC)[CH:11]=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:28][C:29]#[N:30]>>[OH:7][C:8]1[CH:9]=[C:10](/[CH:11]=[C:28](/[C:27]2[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:25]([O:24][CH3:23])[CH:26]=2)\[C:29]#[N:30])[CH:13]=[CH:14][C:15]=1[OH:16]

Participants

3

Reactant 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 11449838HCID 11449838, compound

Product 1

HCID 5896118HCID 5896118, compoundYield 50%

Procedure

The hydroxyl groups of 3,4-dihydroxybenzaldehyde (2.0 g) were protected by use of 2-methoxyethoxymethyl chloride (3.6 g) in accordance with (production process 1), to thereby produce 3,4-bis(methoxyethoxymethoxy)benzaldehyde (3.6 g, yield: 89%). The thus-produced 3,4-bis(methoxyethoxymethoxy)benzaldehyde (3.5 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 (1.6 g, yield: 50%).

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-f9b7df94508a4e67a16445bb5fa2e8ef
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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