Methyl iodide → 2-Chloro-3-methoxybenzaldehyde

HRID 1744294Notes

Reaction equation

HRID 1744294 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5933762-Chloro-3-hydroxybenzaldehyde

Product 1

HCID 125756952-Chloro-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-3-hydroxybenzaldehyde (4.55 g, 29 mmol) in DMF (30 mL) was added K2CO3 (4.8 g, 34.9 mmol) followed by MeI (2.7 mL, 43.6 mmol), and the mixture was stirred at room temperature for 16 hours. Following concentration in vacuo, the residual was taken up in ethyl acetate, washed with H2O, brine, dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel with ethyl acetate/hexanes 1/5 afforded 2-chloro-3-methoxybenzaldehyde 3a (4.68 g, 94%) as a colorless oil, which solidified upon standing. GCMS (EI) m/z 170, 172 (M+).

Workup

  1. concentrationconcentration in vacuo
  2. washwashed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel with ethyl acetate/hexanes 1/5 afforded 2-chloro-3-methoxybenzaldehyde 3a (4.68 g, 94%) as a colorless oil, which

Sources & evidence

ORD record
ord-b677d1f3de8844a9ab6f4abcc584c24f
Source dataset
uspto-grants-2006_03
Patent number
US07015226B2

Reaction notes

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