Potassium Iodide → HCID 3799557, compound

HRID 487673Notes

Reaction equation

HRID 487673 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].[I-].[K+].C[N:21]([CH3:24])C=O>>[C:24]([CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])#[N:21]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 3799557HCID 3799557, compoundYield 90.9%

Procedure

To a cooled mixture of 2-hydroxy-5-methoxybenzaldehyde (500.0 g), potassium carbonate (908.4 g) and potassium iodide (272.8 g) in N,N-dimethylformamide (2.5 l) chloroacetonitrile (297.7 g) was added dropwise over 8 minutes below 10° C. under nitrogen. After being stirred at ambient temperature for 110 minutes, the mixture was poured slowly into ice-water (20 l) and stirred for 2 hours. The precipitates were cooled by centrifugal filtration, washed with water (1 l) 7 times and air-dried at ambient temperature to give 2-cyanomethoxy-5-methoxybenzaldehyde (571.4 g).

Workup

  1. additionwas added dropwise over 8 minutes below 10° C. under nitrogen
  2. stirringstirred for 2 hours
  3. temperatureThe precipitates were cooled by centrifugal filtration
  4. washwashed with water (1 l) 7 times
  5. customair-dried at ambient temperature

Sources & evidence

ORD record
ord-0b90e6a9d43b4632b5a002e147d6b8c1
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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