8-(4-Propylphenyl)-1,4-dioxaspiro[4.5]decan-8-ol → 8-(4-Propylphenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 342349Notes

Reaction equation

HRID 342349 reaction equation
[CH2:1]1[CH2:20][O:19][C:3]2([CH2:8][CH2:7][C:6](O)([C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=3)[CH2:5][CH2:4]2)[O:2]1>C1(C)C=CC=CC=1>[CH2:20]1[CH2:1][O:2][C:3]2([CH2:4][CH:5]=[C:6]([C:9]3[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH3:17])=[CH:13][CH:14]=3)[CH2:7][CH2:8]2)[O:19]1

Participants

3

Reactant 1

HCID 659181288-(4-Propylphenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 675902608-(4-Propylphenyl)-1,4-dioxaspiro[4.5]dec-7-eneYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 500 ml of toluene was dissolved 98 g of the 1,1-ethylenedioxy-4-hydroxy-4-(4-n-propylphenyl)cyclohexane mentioned above, 5 g of Amberlist 15E was added as catalyst thereto, and stirred under a reflux for 2 hours. After the reaction solution was cooled, the catalyst was filtered off. Organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under a reduced pressure to obtain 90 g of 1,1-ethylenedioxy-4-(4-n-propylphenyl)-4-cyclohexene.

Workup

  1. additionwas added as catalyst
  2. temperaturea reflux for 2 hours
  3. temperatureAfter the reaction solution was cooled
  4. filtrationthe catalyst was filtered off
  5. washOrganic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-66d19e8404bc48338104789759baed5f
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Reaction notes

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