Methyl iodide → 5'-Methoxy-spiro(cyclopentane-1,1'-indan)-3'-one

HRID 426916Notes

Reaction equation

HRID 426916 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:6][C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:16][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:6][C:5]2=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 203884005'-Hydroxy-spiro(cyclopentane-1,1'-indan)-3'-one

Product 1

HCID 190364645'-Methoxy-spiro(cyclopentane-1,1'-indan)-3'-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5'-hydroxy-spiro(cyclopentane-1,1'-indan)-3'-one (20.2 g; 0.1 mole), acetone (1000 ml), anhydrous potassium carbonate (37.5 g) and methyl iodide (50 ml) is refluxed for 5-6 hours. The mixture is evaporated to dryness, after which the residue is taken up in water and trichloroethylene. The trichloroetylene solution is extracted with 2×150 ml of 2 N sodium hydroxide and dried with anhydrous magnesium sulphate. The solvent is distilled off and a yellow oil is obtained, which soon crystallizes, yield 16 g (74%). After recrystallization from n-hexane the substance melts at 80° C.

Workup

  1. temperatureis refluxed for 5-6 hours
  2. customThe mixture is evaporated to dryness
  3. extractionThe trichloroetylene solution is extracted with 2×150 ml of 2 N sodium hydroxide
  4. dry with materialdried with anhydrous magnesium sulphate
  5. distillationThe solvent is distilled off
  6. customa yellow oil is obtained
  7. customwhich soon crystallizes
  8. customAfter recrystallization from n-hexane the substance melts at 80° C.

Sources & evidence

ORD record
ord-b09011d9ac1648e6a0c8c4636c00cc49
Source dataset
uspto-grants-1979_10
Patent number
US04172093

Reaction notes

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