Methyl iodide → HCID 66968824, compound

HRID 1362521Notes

Reaction equation

HRID 1362521 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[C:6]([OH:13])[CH:5]=1)([CH3:3])[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66969284HCID 66969284, compound

Product 1

HCID 66968824HCID 66968824, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4′-isopropyl-2′-hydroxyacetophenone (33.4 g, 187.4 mmol) is dissolved in acetone (233 ml). Following addition of K2CO3 (51.8 g, 374.8 mmol) and methyl iodide (23.33 ml, 374.8 mmol) the batch is heated at reflux for three days. The reaction mixture is cooled and filtered through a glass fibre filter and the residue is washed with cold acetone. The solvent is removed and the residue is chromatographed (silica gel, eluent: ethyl acetate/hexane). This isolates 31.85 g (88.4%) of the desired compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for three days
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered through a glass fibre
  5. filtrationfilter
  6. washthe residue is washed with cold acetone
  7. customThe solvent is removed
  8. customthe residue is chromatographed (silica gel, eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b5c19ca90c924696a941695fea43d1cf
Source dataset
uspto-grants-2011_02
Patent number
US07880042B2

Reaction notes

Loading…