Methyl iodide → 2-Chloro-4-methoxybenzaldehyde

HRID 356128Notes

Reaction equation

HRID 356128 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 93617462-Chloro-4-methoxybenzaldehydeYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The reaction mixture of 1.0 g (6.4 mmoles) of 2-chloro-4-hydroxybenzaldehyde, 4.4 g (32 mmoles) of potassium carbonate, and 1.4 g (9.6 mmoles) of methyl iodide in 10 mL of N,N-dimethylformamide was stirred at 70° C. for 2 h and poured into ice water. The precipitate was filtered, washed with water, and dried at 40° C. in vacuum oven overnight to yield 750 mg (68%) of the title compound as a light pink solid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried at 40° C. in vacuum oven overnight

Sources & evidence

ORD record
ord-77313164d9324f9c9e918ab8e5832331
Source dataset
uspto-grants-1998_11
Patent number
US05834504

Reaction notes

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