3-Chloro-2-methyl-1-propene → 4-Methyl-7-methallyloxy-1-indanone

HRID 414683

Reaction equation

HRID 414683 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].[OH-].[K+].[CH2:15](Cl)[C:16](=[CH2:18])[CH3:17]>CO>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][C:16](=[CH2:15])[CH3:18])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 14797Potassium HydroxideHCID 124362447-Hydroxy-4-methyl-1-indanone

Product 1

HCID 136041514-Methyl-7-methallyloxy-1-indanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 15 g of 4-methyl-7-hydroxy-1-indanone and 7.95 g of potassium hydroxide in 200 ml of methanol was added 13.55 ml of methallyl chloride, and the mixture was refluxed by heating for 11 hours. The insoluble matters in the reaction mixture were removed by filtration, then the solvent was removed by evaporation. The residue obtained was purified by means of a silica gel column chromatography (eluent: n-hexane: dichloromethane=1:1) to obtain 9 g of 4-methyl-7-methallyloxy-1-indanone.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 11 hours
  3. customThe insoluble matters in the reaction mixture were removed by filtration
  4. customthe solvent was removed by evaporation
  5. customThe residue obtained
  6. customwas purified by means of a silica gel column chromatography (eluent: n-hexane: dichloromethane=1:1)

Sources & evidence

ORD record
ord-cd8b7b060be64f7289e4470cda2668f0
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Linked notes

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