Water → 2-Chloro-4-methoxybenzaldehyde

HRID 2354282Notes

Reaction equation

HRID 2354282 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.O>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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 93617462-Chloro-4-methoxybenzaldehydeYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-chloro-4-hydroxybenzaldehyde (0.50 g) and potassium carbonate (1.1 g) in N,N-dimethylformamide (5 mL) was added methyl iodide (0.40 mL) at room temperature, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 2-chloro-4-methoxybenzaldehyde (0.54 g). The title compound was prepared in a similar manner to that described in Reference Example 45 using this material instead of 4-isobutyl-benzaldehyde.

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f0b8ec6955a44728b5540d5b5b8ffe31
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

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