p-METHYLACETOPHENONE → p,alpha-DIMETHYLBENZYL ALCOHOL

HRID 1855118

Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[O-]CC.[K+]>CCOCC.C(O)(C)C.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]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 2.6 μmol, 0.33 mol %) were dissolved in ether (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 40° C. After the mixture was cooled to room temperature, p-methylacetophenone (0.8 mmol), ether (2 mL) and a solution of potassium ethoxide in i-propanol (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=1/5). Accordingly, pure 1-(p-methylphenyl)ethanol was obtained and the ee value (ee=99.3%) was measured by GC analysis.

Aufarbeitung

temperatureheated
temperatureAfter the mixture was cooled to room temperature
stirringstirred for 12 h under H2 (10 atm) at 25° C
customThe solvent was removed under reduced pressure
customthe resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/5)

Quellen und Nachweise

ORD-Eintrag: ord-ead8dc1ea0614d72b4c68ceebf430b92
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08962852B2

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