Methanol → 4-methoxy-2,3-dihydro-1H-inden-1-one

HRID 1451327Notes

Reaction equation

HRID 1451327 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[C:12](=O)([O-])[O-].[K+].[K+].CO>CC(C)=O>[CH3:12][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 45474914-methoxy-2,3-dihydro-1H-inden-1-oneYield 79.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-hydroxy-indan-1-one (14.5 g, 0.0979 mol) and 27.08 g (0.195 mol) of potassium carbonate was added 500 ml of acetone and 48.7 ml (0.78 mol) of methanol with stirring and the resulting mixture was heated to reflux for 4 h, cooled, and allowed to stand at room temperature for 10 h. The above mixture was filtered concentrated under vacuo, the solid residue was dissolved in methanol, heated and filtered. The filtrate was concentrated to a volume of 100 ml, cooled and filtered to afford 12.6 g (79%) of 4-methoxy-indan-1-one.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. temperaturecooled
  4. filtrationThe above mixture was filtered
  5. concentrationconcentrated under vacuo
  6. dissolutionthe solid residue was dissolved in methanol
  7. temperatureheated
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated to a volume of 100 ml
  10. temperaturecooled
  11. filtrationfiltered

Sources & evidence

ORD record
ord-d086fcb66084471b915bac811e39c94b
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Reaction notes

Loading…