Potassium Hydroxide → 1-(2-Methoxyphenyl)ethan-1-ol

HRID 1855123Notes

Reaction equation

HRID 1855123 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])[CH3:10].[OH-].[K+]>C1(C)C(C)=CC=CC=1.C1C=CC=CC=1.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([OH:11])[CH3:10]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 684812'-Methoxyacetophenone

Product 1

HCID 1145381-(2-Methoxyphenyl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 10962144Benzeneruthenium(II) Chloride DimerCatalystHCID 7237O-XyleneSolvent2×

Conditions

Temperature
140 °C

Procedure

Benzeneruthenium(II) chloride dimer (1.0 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in xylene (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 140° C. After the mixture was cooled to room temperature, o-methoxyacetophenone (0.4 mmol), xylene (2 mL) and an aqueous solution of potassium hydroxide (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 12 h under H2 (3 atm) at 25° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5). Accordingly, pure (o-methoxyphenyl)ethanol was obtained and the ee value (ee=98%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 12 h under H2 (3 atm) at 25° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)

Sources & evidence

ORD record
ord-58339b2455d044aabdc542dc56d2081e
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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