Methyl iodide → HCID 18690522, compound

HRID 1872442Notes

Reaction equation

HRID 1872442 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]1([C:13](=[O:24])[CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CI>C1(C)C=CC=CC=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:7]1([C:13](=[O:24])[CH:14]([CH3:1])[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14496781HCID 14496781, compound

Product 1

HCID 18690522HCID 18690522, compoundYield 62.6%

Reagents, catalysts & solvents 3

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of 55.2 g anhydrous potassium carbonate, 1.6 g tetrabutylammonium fluoride, 24.8 g 1-phenyl-3-isoheptyl-1,3-propanedione and 150 ml. toluene were stirred and heated to reflux for 2 hours with a Dean-Stark trap under a nitrogen atmosphere. The mixture was cooled to room temperature, 7.0 ml methyl iodide was added and the mixture was heated with stirring to 50 degrees Centigrade overnight. The product was diluted with toluene and water, and the organic phase washed with water, and stripped under reduced pressure. The residue was distilled in a Kugelrohr apparatus at 100-110 degrees Centigrade at 0.3 mm Hg to give 25.6 g distillate. The distillate was purified on a silica gel column and redistilled in a Kugelrohr apparatus to give 16.4 g of 1-phenyl-2-methyl-3-isoheptyl-1,3-propanedione. Employing the same procedure using benzyl iodide will provide the corresponding 1-phenyl-2-benzyl-3-isoheptyl-1,3-propanedione.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours with a Dean-Stark trap under a nitrogen atmosphere
  3. temperaturethe mixture was heated
  4. washthe organic phase washed with water
  5. distillationThe residue was distilled in a Kugelrohr apparatus at 100-110 degrees Centigrade at 0.3 mm Hg
  6. customto give 25.6 g distillate
  7. distillationThe distillate was purified on a silica gel column
  8. distillationredistilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-ba70ecce78a942899de8e0524e7f4211
Source dataset
uspto-grants-2000_08
Patent number
US06107523

Reaction notes

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