1,4-Dioxane → (Z)-2,6-dimethyloct-2-ene-1,8-diol

HRID 1973206Notes

Reaction equation

HRID 1973206 reaction equation
C([O:4][CH2:5][CH2:6][C:7]([CH3:15])=[CH:8][CH2:9][CH2:10][C:11](Cl)([CH3:13])[CH3:12])(=O)C.[H][H].[O:18]1CCOCC1>[Pd]>[OH:18][CH2:12]/[C:11](=[CH:10]\[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5][OH:4])[CH3:15])/[CH3:13]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 537651067-Chloro-3,7-dimethyl-3-octenyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 77134639(Z)-2,6-dimethyloct-2-ene-1,8-diol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1 mole of 7-chloro-3,7-dimethyl-3-octenyl acetate was dissolved into 200 milliliters of dioxane and the solution was subjected to hydrogenation reaction in a reactor containing 20 grams of activated palladium black at about 25° C. under normal pressure until hydrogen was no more absorbed. Then, the palladium black was filtered off from the reaction mixture, and dioxane was distilled off from the filtrate. To the resulting residue were added 50 milliliters of water, 200 milliliters of acetone and 10 grams of silver oxide, and the mixture was heated under reflux for 72 hours. After filtrating off precipitate contained in the reaction mixture, acetone and water were distilled off from the filtrate. By distillation of the residual liquid a fraction boiling in the temperature range of 135°-145° C./4.0mmHg was collected, whereby 0.6 mole of hydroxycitronellol was obtained.

Workup

  1. customthe solution was subjected to hydrogenation reaction in a reactor
  2. customno more absorbed
  3. filtrationThen, the palladium black was filtered off from the reaction mixture, and dioxane
  4. distillationwas distilled off from the filtrate
  5. additionTo the resulting residue were added 50 milliliters of water, 200 milliliters of acetone and 10 grams of silver oxide
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 72 hours
  8. filtrationAfter filtrating off precipitate
  9. distillationwere distilled off from the filtrate
  10. distillationBy distillation of the residual liquid a fraction
  11. customboiling in the temperature range of 135°-145° C./4.0mmHg
  12. customwas collected

Sources & evidence

ORD record
ord-844177c4f8b34aab842e6d912ad051a8
Source dataset
uspto-grants-1976_12
Patent number
US03996303

Reaction notes

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