9-Bromomethylanthracene → Lepidopterene

HRID 1249301

Reaction equation

HRID 1249301 reaction equation
Br[CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.O1[CH2:22][CH2:21]OCC1>CO>[CH2:2]1[C:2]23[C:21]4[C:22](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:5]([CH2:6][C:10]42[C:9]2[C:4]([CH:3]1[C:16]1[C:11]4=[CH:12][CH:13]=[CH:14][CH:15]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:4]1[C:3]3=[CH:16][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 170199-BromomethylanthraceneHCID 312751,4-Dioxane

Product 1

HCID 11361068LepidoptereneYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9-(bromomethyl)anthracene (4 gm., 14.8 mmoles) was dissolved in 200 ml. of dioxane at 70° C. under nitrogen. With the addition of powdered stannous chloride dihydrate (3.2 gm., 14 mmoles), the solution turned orange brown. Coloration faded in a few minutes and the reaction mixture was allowed to stand at 70° C. for another half hour and then was diluted with an equal volume of methanol. The crude yellow-green precipitate was filtered and then dissolved in methylene chloride and the methylene chloride solution filtered to remove undissolved material. The solution was decolored and the lepidopterene reprecipitated from the methylene chloride solution by the addition of methanol to obtain 1 gm. (2.6 mmoles) of the colorless, crystalline solid (18% yield).

Workup

  1. customat 70° C.
  2. waitColoration faded in a few minutes
  3. filtrationThe crude yellow-green precipitate was filtered
  4. dissolutiondissolved in methylene chloride
  5. filtrationthe methylene chloride solution filtered
  6. customto remove undissolved material
  7. customthe lepidopterene reprecipitated from the methylene chloride solution by the addition of methanol
  8. customto obtain 1 gm

Sources & evidence

ORD record
ord-cab4a1f7d52b447ebc32a143d370545f
Source dataset
uspto-grants-1986_12
Patent number
US04629821

Linked notes

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