Hydrazine → 9-(Prop-2-en-1-yl)-9,10-dihydro-9,10-ethanoanthracene

HRID 442526Notes

Reaction equation

HRID 442526 reaction equation
[CH2:1]([C:4]12[CH2:19][C:18](=O)[CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=31)[C:10]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3].NN.[OH-].[Na+]>C(O)COCCOCCO.O>[CH2:1]([C:4]12[CH2:19][CH2:18][CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=31)[C:10]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 68119883HCID 68119883, compound

Product 1

HCID 540335399-(Prop-2-en-1-yl)-9,10-dihydro-9,10-ethanoanthracene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8172Triethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 9-β-propenyl-9,10-dihydro-9,10-ethanoanthracene-11-one (280 mg), hydrazine (0.2 ml) and sodium hydroxide in triethyleneglycol was stirred at 150° C. for 30 minutes and at 190° - 200° C. for 2.5 hours. The reaction mixture was diluted with water and extracted with benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified over silica gel chromatography to give 9-β-propenyl-9,10-dihydro-9,10-ethanoanthracene, M.P. 42° - 43° C.

Workup

  1. extractionextracted with benzene
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified over silica gel chromatography

Sources & evidence

ORD record
ord-a2886c66a7f14d15b1a9e97a4267d117
Source dataset
uspto-grants-1977_08
Patent number
US04045560

Reaction notes

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