Iodine → 1-Propanone, 2-methyl-1-(4-methylphenyl)-

HRID 1679177Notes

Reaction equation

HRID 1679177 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[Mg].II.[C:8]1([CH3:16])[CH:13]=[CH:12][C:11]([C:14]#N)=[CH:10][CH:9]=1.S(=O)(=O)(O)[OH:18]>CCOCC>[CH3:16][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:18])[CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 63582-BromopropaneHCID 7724p-TolunitrileHCID 5462224Magnesium

Product 1

HCID 5768291-Propanone, 2-methyl-1-(4-methylphenyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

24.6 g of 2-bromopropane was added to a mixture of 4.8 g of magnesium, a few crystals of iodine, and 200 ml of ether. To the resulting Grignard reagent was added a solution of 23.4 g of p-tolunitrile in ether, over a 15-minute period at about 30°. The mixture was stirred at room temperature for 32 hours and refluxed for 3 days, then treated with dilute sulfuric acid, cooled and extracted with ether. The ether solution was dried (MgSO4) and stripped of solvent. The resulting liquid product was cooled, unreacted starting material was decanted. The residue was chromatographed (silica gel, methylene chloride) to give 1-(4-methylphenyl)-2-methyl-1-propanone (5A).

Workup

  1. waitover a 15-minute period at about 30°
  2. temperaturerefluxed for 3 days
  3. temperaturecooled
  4. extractionextracted with ether
  5. dry with materialThe ether solution was dried (MgSO4)
  6. temperatureThe resulting liquid product was cooled
  7. customwas decanted
  8. customThe residue was chromatographed (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-66d11cdf3b3f4ccb9ea276a823056f46
Source dataset
uspto-grants-1978_03
Patent number
US04079149

Reaction notes

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