Allyl bromide → 8-Allyloxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051413Notes

Reaction equation

HRID 2051413 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]2[C:14]=1[C:13](=[O:15])[CH:12]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]1.[OH-].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CO>[CH2:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]2[C:14]=1[C:13](=[O:15])[CH:12]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 15157186HCID 15157186, compound

Product 1

HCID 151571908-Allyloxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20.0 Grams of 8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone, 10.4 g of potassium hydroxide and 200 ml of methanol were refluxed under heating until a homogeneous solution was produced. The solution was left to stand and thereto was added 16.0 ml of allyl bromide. The mixture was again refluxed under heating for 3 hours. The reaction mixture was poured into ice water and the separated crystal was collected by filtration and washed with water and then with n-hexane. The thus obtained crystal was once dissolved in chloroform and dried with magnesium sulfate and thereafter the solvent was distilled off. The crystal was recrystallized from ethanol to obtain 14.6 g of 8-allyloxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone.

Workup

  1. temperatureunder heating until a homogeneous solution
  2. customwas produced
  3. waitThe solution was left
  4. temperatureThe mixture was again refluxed
  5. temperatureunder heating for 3 hours
  6. filtrationthe separated crystal was collected by filtration
  7. washwashed with water
  8. dissolutionThe thus obtained crystal was once dissolved in chloroform
  9. dry with materialdried with magnesium sulfate
  10. distillationthe solvent was distilled off
  11. customThe crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-1331178b43dd446a89e72282fa71068f
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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