Potassium Hydroxide → 4-Methyl-7-crotyloxy-1-indanone

HRID 414681

Reaction equation

HRID 414681 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]=[CH:17][CH3:18]>CO>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][CH:16]=[CH:17][CH3:18])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1224142-Butene, 1-bromo-HCID 124362447-Hydroxy-4-methyl-1-indanone

Product 1

HCID 536343704-Methyl-7-crotyloxy-1-indanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 10 g of 4-methyl-7-hydroxy-1-indanone and 5.3 g of potassium hydroxide in 200 ml of methanol was added 8.2 ml of crotyl bromide, and the mixture was refluxed by heating for 4 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 washed with a diluted sodium hydroxide aqueous solution, then washed with water, dried with anhydrous magnesium sulfate, and 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 8.72 g of 4-methyl-7-crotyloxy-1-indanone.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 4 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. washthe chloroform layer was washed with a diluted sodium hydroxide aqueous solution
  8. washwashed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customthe solvent was removed by evaporation
  11. customThe residue obtained
  12. customwas purified by means of a silica gel column chromatography (eluent: n-hexane: dichloromethane=1:1)

Sources & evidence

ORD record
ord-c5e1de5bb72f45a59afd3faaff265cc2
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Linked notes

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