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Ethanol → 2-(Dimethylaminophenylmethyl)cyclohexanol

HRID 459661
Notes
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Reaction equation

HRID 459661 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 112647962-(Dimethylaminophenylmethyl)cyclohexanolYield 86.6%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

3.0 g (13.0 mmole) of the 2-(dimethylaminophenylmethyl)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.

Workup

  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)

Sources & evidence

ORD record
ord-a16547bdb9c349e2a668a951acb9873d
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE039530E1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes