Lithium Hydroxide → 1-(3-Methylphenyl)ethanol

HRID 1855116

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HRID 1855116 반응식
[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

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 114553-Methylacetophenone

생성물 1

HCID 1109521-(3-Methylphenyl)ethanol

시약·촉매·용매 2

HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride촉매HCID 6344Dichloromethane용매2회

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온도
40 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e35b7bdde18749498a7f72716f74c277
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962852B2

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