2-Phenylethanol → HCID 15875395, compound

HRID 429713Notes

Reaction equation

HRID 429713 reaction equation
[C:1]1([CH2:7][CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1>C1CCCCC1>[CH:10]1([O:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 60542-PhenylethanolHCID 136091-Cyclooctene

Product 1

HCID 15875395HCID 15875395, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
83 °C

Procedure

A mixture of 183 g phenylethyl alcohol, 980 g cyclohexane and 14 g AMBERLYST® 15 was heated to reflux (83° C.) with stirring. cyclooctene over a period of 3 hrs. After refluxing for 13 hrs at 83-89° C. the mixture was filtrated and concentrated on a rotatory evaporator at 45° C. and 25 mbar resulting in 233 g concentrate, containing 17% cyclooctene, 58% phenylethyl alcohol and 18% phenylethyl cyclooctyl ether and 2% diphenylethyl ether by GC analysis, which was vacuum distilled. The fraction with a boiling range of 89-103° C. at 0.7 mbar (13 g containing 7% phenylethyl alcohol, 80% phenylethyl cyclooctyl ether and 10% diphenylethyl ether by GC analysis) was subjected to flash column chromatography over silica with a 1:25 diethyl ether/pentane mixture, yielding 5 g phenylethyl cyclooctyl ether of 97.4% purity by GC analysis, nD20=1.5175.

Workup

  1. temperaturewas heated
  2. temperatureAfter refluxing for 13 hrs at 83-89° C. the mixture
  3. filtrationwas filtrated
  4. concentrationconcentrated on a rotatory evaporator at 45° C.
  5. custom25 mbar resulting in 233 g
  6. concentrationconcentrate
  7. additioncontaining 17% cyclooctene, 58% phenylethyl alcohol and 18% phenylethyl cyclooctyl ether and 2% diphenylethyl ether by GC analysis, which
  8. distillationdistilled
  9. additionThe fraction with a boiling range of 89-103° C. at 0.7 mbar (13 g containing 7% phenylethyl alcohol, 80% phenylethyl cyclooctyl ether and 10% diphenylethyl ether by GC analysis)

Sources & evidence

ORD record
ord-a8d4082159fd461a8892e77b26cae536
Source dataset
uspto-grants-2001_11
Patent number
US06319889B1

Reaction notes

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