2,7-Dimethyl-1,3,7-octatriene → Tetrahydronaphthoquinone Isoprene

HRID 2420270Notes

Reaction equation

HRID 2420270 reaction equation
[C:1]1(=[O:12])[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH3:13][C:14]([CH:16]=[CH:17]CCC(C)=C)=[CH2:15]>C1CCCCC1>[C:4]1(=[O:11])[C:5]2[CH:10]([CH2:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:12])[CH2:2][CH2:3]1.[CH2:17]=[CH:16][C:14](=[CH2:13])[CH3:15]

Participants

4

Reactant 2

HCID 5570852,7-Dimethyl-1,3,7-octatrieneHCID 17958094Tetrahydronaphthoquinone

Product 1

HCID 86735968Tetrahydronaphthoquinone IsopreneYield 105.5%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of 101 g (0.623 mole) of tetrahydronaphthoquinone and 110 g (0.81 mole) of 2,7-dimethyl-1,3,7-octatriene in 300 ml cyclohexane was refluxed for 18 hours. After removal of 200 ml solvent, 300 ml of hexane were added. The mixture was then warmed, stirred with powdered charcoal, and filtered. On cooling, 151.3 g of crude product were obtained (81.5% yield). A 3 g analytical sample, after recrystallization from 20 ml hexane, had a mp of 87.5° to 88° C.

Workup

  1. customAfter removal of 200 ml solvent, 300 ml of hexane
  2. additionwere added
  3. temperatureThe mixture was then warmed
  4. filtrationfiltered
  5. temperatureOn cooling

Sources & evidence

ORD record
ord-14fdc9fc52034e8b9284bdf7c524883b
Source dataset
uspto-grants-1978_08
Patent number
US04110353

Reaction notes

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