Phenol, p-(3-methyl-2-butenyl)- → HCID 178444570, compound

HRID 1362826Notes

Reaction equation

HRID 1362826 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.[Al].[CH2:14]([CH:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1)[CH2:15][CH:16]([CH3:18])[CH3:17]>[Fe].[Ni].[Ni].[Fe].O>[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].[CH2:14]([C@H:19]1[CH2:20][CH2:21][C@H:22]([OH:25])[CH2:23][CH2:24]1)[CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

9

Reactant 3

HCID 14543Phenol, p-(3-methyl-2-butenyl)-HCID 5359268AluminumHCID 18356807Cyclohexanol, 4-(3-methylbutyl)-

Product 2

HCID 178444569HCID 178444569, compoundYield 33.1%HCID 178444570HCID 178444570, compoundYield 66.3%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 23925IronCatalystHCID 10080372Iron--nickel (1/1)CatalystHCID 962WaterSolvent

Procedure

165 g 4-(3-methyl-but-2-enyl)-phenol, 2 wt. % Raney nickel-iron (composition of the catalyst: 45% nickel, 3% aluminium, 8% iron; water content 44%) are initially introduced into a stirred autoclave with a gassing stirrer. Hydrogenation is carried out for 6 hours at 170° C. under a hydrogen pressure of 20 bar. After filtration, 165 g of crude product are obtained. 158 g 4-isoamylcyclohexanol (b.p.: 65° C., 0.6 mbar), which has the following composition: 33.1% cis-4-isoamylcyclohexanol and 66.3% trans-4-isoamylcyclohexanol, are obtained by distillation of the crude product.

Workup

  1. filtrationAfter filtration, 165 g of crude product
  2. customare obtained

Sources & evidence

ORD record
ord-3535ff07d7e24725801936f5229e156c
Source dataset
uspto-grants-2011_02
Patent number
US07884065B2

Reaction notes

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