4-Methylphenethyl alcohol → p-METHYL PHENYLETHYL CYCLOHEXYL ETHER

HRID 1902185Notes

Reaction equation

HRID 1902185 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1>C1CCCCC1>[CH:2]1([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 952944-Methylphenethyl alcohol

Product 1

HCID 20508517p-METHYL PHENYLETHYL CYCLOHEXYL ETHER

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
110 °C

Procedure

246 grams of cyclohexane 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-d52b541218314a078894ccfa0bbf46c0
Source dataset
uspto-grants-1982_12
Patent number
US04362657

Reaction notes

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