Cyclohexene → p-METHYL PHENYLETHYL CYCLOHEXYL ETHER

HRID 66712Notes

Reaction equation

HRID 66712 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1>>[CH:1]1([O:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 8079CyclohexeneHCID 952944-Methylphenethyl alcohol

Product 1

HCID 20508517p-METHYL PHENYLETHYL CYCLOHEXYL ETHER

Conditions

Temperature
110 °C

Procedure

246 grams of cyclohexene is added to a stirred slurry of p-methyl phenyl beta ethanol (408 grams) and 25 grams of Amberlyst® 15 cation exchange resin maintained at 110° C., over a 2 hour period. The reaction mass is then aged at 110° C. for an additional 3 hours whereupon it is cooled and filtered. The resulting solution is then heated at reflux with 80 grams of 30% aqueous sodium hydroxide. The reaction mass is then cooled and the resulting organic layer is washed with 1 liter of water. The organic layer is separated from the reaction mass and distilled through a 11/2"×12" Goodlow packed column to afford the following distillation fractions:

Workup

  1. temperatureis cooled
  2. filtrationfiltered
  3. temperatureThe resulting solution is then heated
  4. temperatureat reflux with 80 grams of 30% aqueous sodium hydroxide
  5. temperatureThe reaction mass is then cooled
  6. washthe resulting organic layer is washed with 1 liter of water
  7. customThe organic layer is separated from the reaction mass
  8. distillationdistilled through a 11/2"×12" Goodlow
  9. customto afford
  10. distillationthe following distillation fractions

Sources & evidence

ORD record
ord-c3b719ec433f427ebb3bdfb60e0f9c82
Source dataset
uspto-grants-1982_08
Patent number
US04343791

Reaction notes

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