Allyl bromide → 4-Methyl-7-allyloxy-1-indanone

HRID 414679

Reaction equation

HRID 414679 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](Br)[CH:16]=[CH2:17]>CO>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][CH:16]=[CH2:15])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 124362447-Hydroxy-4-methyl-1-indanone

Product 1

HCID 136041474-Methyl-7-allyloxy-1-indanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 36 g of 4-methyl-7-hydroxy-1-indanone and 17.6 g of potassium hydroxide in 650 ml of methanol was added 25 ml of allyl bromide, and the mixture was refluxed by heating for 6 hours. The insoluble matters in the reaction mixture were removed by filtration, then the solvent was removed by evaporation. The residue obtained was extracted with chloroform-water, and the chloroform layer was collected by separation, then the solvent was removed by evaporation. The residue thus obtained was washed with ether and purified by means of a column chromatography to obtain 32 g of 4-methyl-7-allyloxy-1-indanone.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 6 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. extractionwas extracted with chloroform-water
  7. customthe chloroform layer was collected by separation
  8. customthe solvent was removed by evaporation
  9. customThe residue thus obtained
  10. washwas washed with ether
  11. custompurified by means of a column chromatography

Sources & evidence

ORD record
ord-2371e098b30d4753b8b9758abde13125
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Linked notes

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