4'-Methoxyacetophenone → 1-(4-Methoxyphenyl)ethanol

HRID 1855124

Reaction equation

HRID 1855124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ru+2].[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 74764'-MethoxyacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 1011481-(4-Methoxyphenyl)ethanol

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 84971Tris(triphenylphosphine)ruthenium(II) dichlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

Tris(triphenylphosphine)ruthenium(II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Fe, R=i-Pr, Ar=3,5-Me2C6H3—, 1.3 μmol, 0.33 mol %) were dissolved in tetrahydrofuran (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 65° C. After the mixture was cooled to room temperature, p-methoxyacetophenone (0.4 mmol), tetrahydrofuran (2 mL) and an aqueous solution of sodium bicarbonate (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 (20 atm) at 40° 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 1-(p-methoxyphenyl)ethanol was obtained and the ee value (ee=99.1%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 12 h under H2 (20 atm) at 40° 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-5971e69ee731422095a4c1a39626804d
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Linked notes

Loading…