Iodine → (2,4,6-Trimethylphenyl)furan-2-ylmethanol

HRID 407842Notes

Reaction equation

HRID 407842 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1Br.[Mg].II.[CH:14](=[O:20])[C:15]1[O:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:14]([C:15]1[O:19][CH:18]=[CH:17][CH:16]=1)[OH:20]

Participants

6

Reactant 4

HCID 807IodineHCID 7362FurfuralHCID 684732-BromomesityleneHCID 5462224Magnesium2×

Product 1

HCID 49962474(2,4,6-Trimethylphenyl)furan-2-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,4,6-trimethyl-1-bromobenzene (30.9 g, 155 mmol) in tetrahydrofuran (100 ml) is added slowly to magnesium turnings (3.77 g, 155 mmol), until the magnesium is just covered. A small quantity of iodine is added and the mixture is allowed to stand at room temperature for 25 minutes and then heated and stirred until the brown colour is lost. The remainder of the aryl bromide solution is added dropwise over a 20 minute period, with occasional heating to maintain the formation of the Grignard reagent solution. The reaction is stirred at room temperature for 1 hour. A solution of furfural (12.8 ml, 155 mmol) in tetrahydrofuran (70 ml) is added dropwise, and once the addition is complete, the reaction is stirred at room temperature for 2 hours. The reaction is quenched by cautious addition of excess saturated ammonium chloride solution, then extracted into ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography on silica gel affords (2,4,6-trimethylphenyl)furan-2-ylmethanol.

Workup

  1. temperatureheated
  2. temperaturewith occasional heating
  3. stirringThe reaction is stirred at room temperature for 1 hour
  4. additiononce the addition
  5. stirringthe reaction is stirred at room temperature for 2 hours
  6. customThe reaction is quenched by cautious addition of excess saturated ammonium chloride solution
  7. extractionextracted into ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-da748a0a4d6a48dbb64278b02f221ed1
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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