3',4',5'-Trimethoxyacetophenone → 1-(3,4,5-trimethoxyphenyl)ethanol

HRID 1855135Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].CC(C)([O-])C.[Na+]>C(O)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]>[CH3:15][O:14][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in ethanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 80° C. After the mixture was cooled to room temperature, 3,4,5-trimethoxyacetophenone (0.4 mmol), ethanol (2 mL) and a solution of sodium t-butoxide in ethanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 48 h under H2 (10 atm) at 0° 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-(3,4,5-trimethoxyphenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

Workup

temperatureheated
temperatureAfter the mixture was cooled to room temperature
stirringstirred for 48 h under H2 (10 atm) at 0° 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)

Sources & evidence

ORD record: ord-1b6fced9cc98410d94c1a0142a2770f0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962852B2

Reaction notes

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