Sodium Iodide → HCID 21946174, compound

HRID 2217073Notes

Reaction equation

HRID 2217073 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][CH2:21][CH3:22]>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][CH2:21][CH3:22])[CH:13]=[O:14]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8002Butyl bromideHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 21946174HCID 21946174, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Anhydrous potassium carbonate (5.9 g, 0.0434 mmol) and sodium iodide (0.434 g, 2.9 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 butyl bromide (3.11 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 2.25 g (58%) of 3-hydroxy-4-butoxybenzaldehyde 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-74ac5ae355f14cf39d0c51e0412283b3
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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