1-Phenylethanol, (R)- → (αR)-α-Methylcyclohexanemethanol

HRID 1890140Notes

Reaction equation

HRID 1890140 reaction equation
[CH3:1][C@@H:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(C)C>[CH:3]1([C@H:2]([OH:9])[CH3:1])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 6375161-Phenylethanol, (R)-

Product 1

HCID 10290808(αR)-α-MethylcyclohexanemethanolYield 88.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An autoclave was charged with (R)-alpha-methylbenzyl alcohol (980 g, synthesized as above) and isopropanol (100 g). Catalyst RuO2.H2O (0.2 g) was then added, and the reaction mixture was hydrogenated at a pressure of 20 bar and a temperature ranging from 70 to 80° C. for 4 hours. The catalyst was filtered. The organic layer was distilled first at 100 mmHg to remove isopropanol, and then at 5-10 mmHg to provide (R)-1-cyclohexylethanol (913 g) (optical rotation: [α]D−4.31°; optical purity: 83.3% ee).

Workup

  1. filtrationThe catalyst was filtered
  2. distillationThe organic layer was distilled first at 100 mmHg
  3. customto remove isopropanol

Sources & evidence

ORD record
ord-84b9db69af7443068733af2b258973c4
Source dataset
uspto-grants-2013_08
Patent number
US08506943B2

Reaction notes

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