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Ethanol → 2-(Dimethylaminophenylmethyl)cyclohexanol

HRID 1596031
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1596031
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 112647962-(Dimethylaminophenylmethyl)cyclohexanolAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e5ae0245ecf44353a171709c1a3a409b
Quelldatensatz
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06288278B1

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