Methyl iodide → HCID 13561782, compound

HRID 1380370Notes

Reaction equation

HRID 1380370 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:20][O:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13561781HCID 13561781, compound

Product 1

HCID 13561782HCID 13561782, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 50 ml of acetone was dissolved 2.17 grams of 4-(7-hydroxy-2-fluorenyl)-butan-2-one, then 1.43 grams of potassium carbonate (anhydrous) was added, and heated to reflux for 2 hours after addition of an excess of methyl iodide. The mixture was stirred at room temperature for overnight and acetone was removed by evaporation in vacuo. The residue was dissolved in ethyl acetate, washed with water, dried with magnesium sulfate, and ethyl acetate was removed therefrom by evaporation in vacuo. The residue was subjected to a silica gel column chromatography, eluted with a 4:1 mixture of n-hexane and ethyl acetate, and the resulting crystals were recrystallized from methanol to give 1.15 grams of 4-(7-methoxy-2-flourenyl)-butan-2-one, white crystals, m.p. 100°-101° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customacetone was removed by evaporation in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate, and ethyl acetate
  7. customwas removed
  8. customby evaporation in vacuo
  9. washeluted with a 4:1 mixture of n-hexane and ethyl acetate
  10. customthe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-a800bfa181a344b29d5ea6d0ee1b7264
Source dataset
uspto-grants-1986_04
Patent number
US04581377

Reaction notes

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