4-Vinyl-1-cyclohexene → 1-Butyl-1,2,3,4-tetrahydroanthracene-9,10-dione

HRID 1973864Notes

Reaction equation

HRID 1973864 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[CH2:13]=[CH:14][CH:15]1[CH2:20][CH:19]=[CH:18][CH2:17][CH2:16]1.[H][H]>[Pd].O1CCOCC1>[CH2:16]([CH:17]1[C:10]2[C:11](=[O:12])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:8])[C:9]=2[CH2:20][CH2:19][CH2:18]1)[CH2:15][CH2:14][CH3:13]

Participants

6

Reactant 3

HCID 74994-Vinyl-1-cyclohexeneHCID 85301,4-NaphthoquinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 214906221-Butyl-1,2,3,4-tetrahydroanthracene-9,10-dioneYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 78.0 g. (0.495 mole) naphthoquinone and 56.0 g. (0.52 mole) butadiene dimer in 200 ml. dioxane was heated at 90°-95° C. for 1 hour, and then at 80°-90° C. for 3 hours. The solution was then cooled and 2.0 g. 10% palladium-on-charcoal (Pd/C) catalyst added. The mixture was then hydrogenated at 42 psi until the theoretical amount of hydrogen was taken up. After removal of the catalyst by filtration and addition of 2 ml. DBN, a slow stream of air was blown through the solution for 6 hours. The solution was then poured into 2000 ml. water and the mixture extracted three times with 300 ml., 100 ml. portions of cyclohexane. The combined cyclohexane extracts were dried over anhydrous potassium carbonate, treated with Darco activated charcoal (Atlas Chemical Industries), and then filtered. After removal of the solvent by using a steam bath, 73.0 g. of crude product was obtained (59% yield). The product was purified by chromatography on acidic alumina using cyclohexane eluent. An analytical sample, after recrystallization from methanol, had m.p. 64°-65° C.

Workup

  1. temperatureThe solution was then cooled
  2. customAfter removal of the catalyst
  3. filtrationby filtration and addition of 2 ml
  4. waitDBN, a slow stream of air was blown through the solution for 6 hours
  5. additionThe solution was then poured into 2000 ml
  6. extractionwater and the mixture extracted three times with 300 ml
  7. dry with materialThe combined cyclohexane extracts were dried over anhydrous potassium carbonate
  8. additiontreated with Darco activated charcoal (Atlas Chemical Industries)
  9. filtrationfiltered
  10. customAfter removal of the solvent
  11. customof crude product was obtained (59% yield)
  12. customThe product was purified by chromatography on acidic alumina
  13. customAn analytical sample, after recrystallization from methanol

Sources & evidence

ORD record
ord-6dbfbd4cffe5493192035f0eef073ac9
Source dataset
uspto-grants-1976_12
Patent number
US03998937

Reaction notes

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