Water → 3-Hydroxy-2-methoxybenzaldehyde

HRID 1178464Notes

Reaction equation

HRID 1178464 reaction equation
[OH: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+].IC.O>CN(C=O)C>[OH:10][C:9]1[C:2]([O:1][CH3:11])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 118049533-Hydroxy-2-methoxybenzaldehydeYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydroxybenzaldehyde (1.00 g, 7.24 mmol), potassium carbonate (1.00 g, 7.24 mmol) and iodomethane (0.59 ml, 1.34 g, 9.4 mmol) in dry DMF (10 ml) were stirred at ambient temperature for 19 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The ethyl acetate layer was extracted with 1N aqueous sodium hydroxide (3×). The basic extracts were combined and acidified by addition of 3N hydrochloric acid, then extracted with ethyl acetate. The ethyl acetate layer was washed with water (4×), brine and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 3-hydroxy-2-methoxy-benzaldehyde (0.68 g, 62%) as a yellowish-tan solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate layer was extracted with 1N aqueous sodium hydroxide (3×)
  4. additionacidified by addition of 3N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water (4×), brine
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3fd10b02782141bea9554be1c1d7df18
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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