Sodium Iodide → 3-Hydroxy-4-propoxybenzaldehyde

HRID 2217071Notes

Reaction equation

HRID 2217071 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:13]=[O:14].[CH2:19](Br)[CH2:20][CH3:21]>CC(=O)CC.O>[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH3:21])[CH:13]=[O:14]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 78401-BromopropaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 219461763-Hydroxy-4-propoxybenzaldehydeYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Anhydrous potassium carbonate (5.9 g, 0.043 mmol) and sodium iodide (0.434 g, 4.3 mmol) were added to 3,4-dihydroxybenzaldehyde (4.0 g, 28.9 mmol), in butanone (100 ml), at room temperature. The reaction was stirred for 10 min after which propyl bromide (2.628 ml, 28.9 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 (3×50 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 1.21 g (23.3%) of 3-hydroxy-4-propoxybenzaldehyde as an off-white solid.

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction was refluxed for 3 h
  3. extractionthe product was extracted with dichloromethane (3×50 ml)
  4. dry with materialthe combined organic layers were dried over magnesium sulphate
  5. customPurification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Sources & evidence

ORD record
ord-da14e69926e54c4ca280e7d37e8537b6
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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