Lithium Hydroxide → 1-(3-Methylphenyl)ethanol

HRID 1855116

反応式

HRID 1855116 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>ClCCl.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:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 114553-Methylacetophenone

生成物 1

HCID 1109521-(3-Methylphenyl)ethanol

試薬・触媒・溶媒 2

HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
40 °C

実験手順

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 dichloromethane (3 mL) under nitrogen atmosphere, and then heated and stirred for 0.5 h at 40° C. After the mixture was cooled to room temperature, m-methylacetophenone (0.4 mmol), dichloromethane (2 mL) and an aqueous solution of lithium hydroxide (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (20 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-(m-methylphenyl)ethanol was obtained and the ee value (ee=99.0%) was measured by GC analysis.

後処理

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (20 atm) at 0° 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)

出典と根拠

ORDレコード
ord-e35b7bdde18749498a7f72716f74c277
出典データセット
uspto-grants-2015_02
特許番号
US08962852B2

関連ノート

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