Hexane → 1-(Propan-2-yl)anthracene

HRID 972162Notes

Reaction equation

HRID 972162 reaction equation
[CH2:1]([C:4]1[C:17]2[C:8](=[CH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1)[CH:2]=C.[CH3:18]CCCCC>[Pd]>[CH:1]([C:4]1[C:17]2[C:8](=[CH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1)([CH3:18])[CH3:2]

Participants

4

Reactant 2

HCID 8058HexaneHCID 14252116HCID 14252116, compound

Product 1

HCID 214059841-(Propan-2-yl)anthracene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a 500 milliliter hydrogenation bottle was placed 0.2 grams of 5% palladium on carbon, 10 grams of 1-(2-propenyl) anthracene and 200 milliliters of hexane and the bottle flushed three times with hydrogen. Hydrogen was fed into the bottle at an initial pressure of 23 pounds per square inch which after 3 days had a final pressure of 19 pounds per square inch. The mixture was filtered, evaporated to an oil and chromatographed on basic alumina with hexane. The mixture was washed with a 10:1 mixture of hexane and benzene and distilled to recover a fraction of pure isopropyl anthracene having a melting point of 36°-36.5° C.

Workup

  1. customthe bottle flushed three times with hydrogen
  2. customafter 3 days
  3. filtrationThe mixture was filtered
  4. customevaporated to an oil
  5. customchromatographed on basic alumina with hexane
  6. washThe mixture was washed with a 10:1 mixture of hexane and benzene
  7. distillationdistilled
  8. customto recover a fraction of pure isopropyl anthracene having a melting point of 36°-36.5° C.

Sources & evidence

ORD record
ord-423aa522fe0242b1a0173588a9829a1c
Source dataset
uspto-grants-1977_10
Patent number
US04052205

Reaction notes

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