Potassium Carbonate → 2-Chloro-3-methoxybenzaldehyde

HRID 1790075Notes

Reaction equation

HRID 1790075 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+]>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

4

Reactant 2

HCID 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 Mel (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-b9cc9e9f66774e30af6bf5dc8409bbea
Source dataset
uspto-grants-2006_07
Patent number
US07071200B2

Reaction notes

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