Water → 2-Chloro-4-methoxybenzaldehyde

HRID 1157529Notes

Reaction equation

HRID 1157529 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:13]I.O>CN(C)C=O>[Cl:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 93617462-Chloro-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To suspension of sodium hydride (2.6 g; 62.6% in oil) in dimethylformamide (80 ml), a solution of 2-chloro-4-hydroxybenzaldehyde (10.0 g) in dimethylformamide (50 ml) was dropped over 15 minutes. The mixture was stirred for 30 minutes. Methyl iodide (4.2 ml) was dropped into the reaction mixture over 10 minutes at 0° C., and stirred for 1 hour. The reaction mixture was poured into water and extracted with hexane/ethyl:acetate (1:1) The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (10.7 g) having the following physical data.

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with hexane/ethyl
  3. washacetate (1:1) The organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4def50e1fe1d4405bd509d00814d1774
Source dataset
uspto-grants-2010_10
Patent number
US07807688B2

Reaction notes

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