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Ethanol → 2-(Dimethylaminophenylmethyl)cyclohexanol

HRID 1596031
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HRID 1596031 반응식
[CH3:1][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.C(O)C.O>C1(C)C=CC=CC=1>[CH3:3][N:2]([CH:4]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])[CH3:1]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 702EthanolHCID 962WaterHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanoneHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 112647962-(Dimethylaminophenylmethyl)cyclohexanol수율 86.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

3.0 g (13.0 mmole) of the 2-(dimethylaminophenyl-methyl)cyclohexanone prepared according to Example 1 (2nd stage), dissolved in 26 ml toluene, were added dropwise to 26 ml (39 mmole) diisobutylaluminium hydride (1.5 M in toluene) at RT under nitrogen. The mixture was heated under reflux for 15 hours, while stirring. For working up, 13 ml ethanol and 13 ml water were slowly added dropwise and the suspension was stored at 0° C. for several hours, filtered through a glass frit and washed several times with a little toluene. The filtrate was concentrated on a rotary evaporator (500 to 10 mbar) and residues of solvent were removed under a high vacuum (approx. 0.1 mbar). 2.62 g (86.6% of theoretical) 2-(dimethylaminophenylmethyl)-cyclohexanol were obtained.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. waitthe suspension was stored at 0° C. for several hours
  4. filtrationfiltered through a glass frit
  5. washwashed several times with a little toluene
  6. concentrationThe filtrate was concentrated on a rotary evaporator (500 to 10 mbar) and residues of solvent
  7. customwere removed under a high vacuum (approx. 0.1 mbar)

출처 및 근거

ORD 기록
ord-e5ae0245ecf44353a171709c1a3a409b
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06288278B1

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