Dimethylformamide → 2-Formyl-5-methoxybenzonitrile

HRID 343936Notes

Reaction equation

HRID 343936 reaction equation
C([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5](F)[CH:4]=1)#N.[CH3:12][O-:13].[Na+].[CH3:15][N:16](C)C=O>CO.O>[C:15]([C:5]1[CH:4]=[C:3]([O:13][CH3:12])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])#[N:16]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27831503-Fluoro-4-formylbenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 468353422-Formyl-5-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-cyano-2-fluorobenzaldehyde (0.5 g, 3.4 mmol) in dry dimethylformamide (3 ml) cooled to 5° C. under a nitrogen atmosphere, a solution of freshly prepared sodium methoxide in methanol (1.41M, 2.62 ml) was added slowly, dropwise. After addition, the reaction mixture was stirred at room temperature for 22 hours. A few drops of water were then added and the turbid solution filtered through celite. The filtrate was further diluted with water until crystallisation commenced to give 2-cyano-4-methoxybenzaldeyde as a pale yellow solid. A second crop was recovered from the filtrate.

Workup

  1. additionAfter addition
  2. filtrationthe turbid solution filtered through celite
  3. additionThe filtrate was further diluted with water until crystallisation

Sources & evidence

ORD record
ord-488d4de933b948b8b02d2e9cbb78fd9a
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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