Water → HCID 178444569, compound

HRID 1362828Notes

Reaction equation

HRID 1362828 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.O.CS(O)(=O)=O>[Rh].C(O)(C)C>[CH2:4]([C@@H:5]1[CH2:6][CH2:7][C@H:8]([OH:11])[CH2:9][CH2:10]1)[CH2:3][CH:2]([CH3:12])[CH3:1].[CH2:4]([C@H:5]1[CH2:6][CH2:7][C@H:8]([OH:11])[CH2:9][CH2:10]1)[CH2:3][CH:2]([CH3:12])[CH3:1]

Participants

7

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 14543Phenol, p-(3-methyl-2-butenyl)-

Product 2

HCID 178444569HCID 178444569, compoundYield 67.6%HCID 178444570HCID 178444570, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 3776IsopropanolSolvent

Procedure

85 g 4-(3-methyl-but-2-enyl)-phenol, 3 wt % rhodium-on-active charcoal (Rh content, based on the weight of the dry catalyst: 5%; water content about 50%) are initially introduced into 500 ml isopropanol and 9.6 g methanesulfonic acid in a stirred autoclave with a gassing stirrer. Hydrogenation is carried out for 5 hours at 80° C. under a hydrogen pressure of 10 bar. After filtration, 85 g 4-isoamylcyclohexanol are obtained as a crude product. After distillation, 80 g 4-isoamylcyclohexanol, which has the following composition: 67.6% cis-4-isoamylcyclohexanol and 31.8% trans-4-isoamylcyclohexanol, are obtained.

Workup

  1. filtrationAfter filtration, 85 g 4-isoamylcyclohexanol
  2. customare obtained as a crude product
  3. distillationAfter distillation, 80 g 4-isoamylcyclohexanol, which

Sources & evidence

ORD record
ord-1808c42d3c3d440fb0d4e97656e3deed
Source dataset
uspto-grants-2011_02
Patent number
US07884065B2

Reaction notes

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