Water → 2-Ethoxy-3-hydroxybenzaldehyde

HRID 1243692Notes

Reaction equation

HRID 1243692 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(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19].O>CN(C=O)C>[CH2:18]([O:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 106786312-Ethoxy-3-hydroxybenzaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydroxybenzaldehyde (1.12 g, 8.11 mmol), potassium carbonate (1.12 g, 8.11 mmol) and iodoethane (0.65 mL, 1.26 g. 8.11 mmol) in dry DMF (10 mL) were stirred at ambient temperature for 21 h. The reaction mixture was poured into water and extracted with diethyl ether. The ether layer was washed with water (2×), and extracted with 1N sodium hydroxide solution (3×). The basic extracts were combined and acidified by addition of 3N hydrochloric acid, then extracted with diethyl ether. The ether layer was washed with water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-ethoxy-3-hydroxybenzaldehyde (0.74 g, 55%) as an orange solid.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether layer was washed with water (2×)
  3. extractionextracted with 1N sodium hydroxide solution (3×)
  4. additionacidified by addition of 3N hydrochloric acid
  5. extractionextracted with diethyl ether
  6. washThe ether layer was washed with water (2×), brine (1×)
  7. dry with materialdried over MgSO4
  8. filtrationAfter filtration
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eeb19656b85f4ff1b0227609c6e4a26e
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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