2'-Hydroxyacetophenone → HCID 10866399, compound

HRID 1855129Notes

Reaction equation

HRID 1855129 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:10])[CH3:9]

Participants

4

Reactant 2

HCID 83752'-HydroxyacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 10866399HCID 10866399, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
140 °C

Procedure

Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=Ph, Ar=C6H5—, 1.3 μmol, 0.33 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-hydroxyacetophenone (0.4 mmol), xylene (2 mL) and an aqueous solution of sodium 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 (10 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=1/2). Accordingly, pure 1-(o-hydroxylphenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 12 h under H2 (10 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=1/2)

Sources & evidence

ORD record
ord-f2285f05e25948689a7f3c1d99e8a1a7
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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