Iodoethane → 4-Ethoxy-3-hydroxybenzaldehyde

HRID 2217060Notes

Reaction equation

HRID 2217060 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12].[CH2:17](I)[CH3:18]>CC(=O)CC.O>[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH:11]=[O:12]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 756794-Ethoxy-3-hydroxybenzaldehydeYield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Anhydrous potassium carbonate (2.25 g, 16.3 mmol) was added to 3,4-dihydroxybenzaldehyde (1.5 g, 10.8 mmol), in butanone (30 ml), at room temperature. The reaction was stirred for 10 min after which ethyl iodide (0.872 ml, 10.8 mmol) was added dropwise and the reaction was refluxed for 3 h. The reaction mixture was diluted with water and the product was extracted with dichloromethane (3×25 ml), the combined organic layers were dried over magnesium sulphate and reduced in vacuo. Purification by column chromatography (SiO2, petroleum:ether (40:60, v/v) with an increasing gradient of ethyl acetate) afforded 0.78 g (43%) of 3-hydroxy-4-ethoxybenzaldehyde as a white solid.

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction was refluxed for 3 h
  3. extractionthe product was extracted with dichloromethane (3×25 ml)
  4. dry with materialthe combined organic layers were dried over magnesium sulphate
  5. customPurification by column chromatography (SiO2, petroleum:ether (40:60

Sources & evidence

ORD record
ord-b10c23fa85de443ba5ef8e98dc6e6e5b
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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