Cyanide → 3,4-Dimethoxybenzene-1-carbonyl cyanide

HRID 404529Notes

Reaction equation

HRID 404529 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[C:14](#[N:16])C.[C-]#N>C1(C)C=CC=CC=1.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([C:14]#[N:16])=[O:7]

Participants

6

Reactant 3

HCID 5975CyanideHCID 6342AcetonitrileHCID 77070Veratroyl chloride

Product 1

HCID 2694353,4-Dimethoxybenzene-1-carbonyl cyanide

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent2×

Procedure

A well stirred mixture [paddle stirrer] of 3,4-dimethoxybenzoyl chloride [AcrosOrganics] (14.05 g; 0.070 mol), dry toluene (32 cm3), dry acetonitrile (8.0 cm3), copper I cyanide (8.5; 0.095 mol) and Celite (5 g) was heated under reflux until no acid chloride remained (−1.5 hrs). The dark reaction mixture was cooled to ˜70° and diluted with toluene (150 cm3). After stirring for an additional ˜30 minutes, the resulting slurry was filtered through a bed of chromatographic silica gel (˜2.5 cm) and the pale yellow filtrate evaporated in vacuo to constant weight to give the title compound as a lemon yellow solid. Yield=11.41 g (85.3%), Mpt=143-145° C. The product was used directly in next stage.

Workup

  1. temperaturewas heated
  2. custom(−1.5 hrs)
  3. customThe dark reaction mixture
  4. temperaturewas cooled to ˜70°
  5. filtrationthe resulting slurry was filtered through a bed of chromatographic silica gel (˜2.5 cm)
  6. customthe pale yellow filtrate evaporated in vacuo to constant weight

Sources & evidence

ORD record
ord-fc8a41c942e243a5aafe4bf5bb46ca39
Source dataset
uspto-grants-2014_06
Patent number
US08748599B2

Reaction notes

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