Tyrosol → 4-(2-Hydroxyethyl)cyclohexan-1-ol

HRID 2403537

Reaction equation

HRID 2403537 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.O.O.O.O.O.O.O.O.O.O.B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]>[Pd].C(O)(C)C>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 10393TyrosolHCID 86618040Sodium tetraborate decahydrate; Solubor; Solubor DF; Three Elephant; Tincal

Product 1

HCID 137511534-(2-Hydroxyethyl)cyclohexan-1-olYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

In a 1 L reactor are successively introduced: 50 g (362 mmol) of 4-(2-hydroxyethyl)phenol, 5 g (13.6 mmol) of sodium tetraborate decahydrate, 500 mL of isopropanol, 5 g of palladium (10% on charcoal washed with isopropanol). The vessel is closed, purged three times with nitrogen and three times with hydrogen. The mixture is stirred for 22 hours under 10 bar pressure of hydrogen at 80° C., cooled back to room temperature, filtered over a celite pad and rinsed with isopropanol. Filtrate is concentrated under reduced pressure, toluene (100 mL) is added and evaporated under reduced pressure. This last procedure being repetited to remove trace amount of isopropanol and gives 52 g (99% yield) of 4-(2-hydroxyethyl)cyclohexanol as a clear viscous oil.

Workup

  1. additionIn a 1 L reactor are successively introduced
  2. customThe vessel is closed
  3. custompurged three times with nitrogen and three times with hydrogen
  4. temperaturecooled back to room temperature
  5. filtrationfiltered over a celite pad
  6. washrinsed with isopropanol
  7. concentrationFiltrate is concentrated under reduced pressure, toluene (100 mL)
  8. additionis added
  9. customevaporated under reduced pressure
  10. customto remove trace amount of isopropanol

Sources & evidence

ORD record
ord-fe26c71de3ea47979839e2f3cd5254de
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Linked notes

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