3,4-Dimethoxybenzeneacetonitrile → HCID 10378984, compound

HRID 2222326Notes

Reaction equation

HRID 2222326 reaction equation
COCCOC[O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:21][C:22]#[N:23]>>[CH3:16][O:17][C:18]1[CH:19]=[C:20](/[C:21](=[CH:10]/[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[OH:7])/[C:22]#[N:23])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

3

Reactant 2

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 196897612-[(2-Methoxyethoxy)methoxy]benzaldehyde

Product 1

HCID 10378984HCID 10378984, compoundYield 52.3%

Procedure

The hydroxyl group of 2-hydroxybenzaldehyde (3.0 g) was protected by use of 2-methoxyethoxymethyl chloride (3.1 g) in accordance with (production process 1), to thereby produce 2-methoxyethoxymethoxybenzaldehyde (3.7 g, yield: 70%). The thus-produced 2-methoxyethoxymethoxybenzaldehyde (2.0 g) and 3,4-dimethoxybenzyl cyanide (1.7 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 (1.4 g, yield: 52%).

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-d9bb4fc1d57e4392b53d83f912cc6aac
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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