2-tert-Butyl-4-methylphenol → Cyclohexanol, 2-(1,1-dimethylethyl)-4-methyl-

HRID 845196Notes

Reaction equation

HRID 845196 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Ru+3].[OH-].[OH-].O1CCOCC1>[C:1]([CH:5]1[CH2:10][CH:9]([CH3:11])[CH2:8][CH2:7][CH:6]1[OH:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 170042-tert-Butyl-4-methylphenol

Product 1

HCID 106739Cyclohexanol, 2-(1,1-dimethylethyl)-4-methyl-Yield 96%

Reagents, catalysts & solvents 2

HCID 12063742Ruthenium(3+) trihydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 400 g (2.44 moles) of 2-tert-butyl-4-methylphenol, 400 ml of dioxane and 1 g of ruthenium hydroxide was initially taken in an autoclave and hydrogenated at 120° C. and under a hydrogen pressure of 50 bar until the pressure remained constant (total hydrogenation time about 3 1/2 hours). The catalyst was separated off, after which the dioxane was distilled off and the residue was fractionated under 0.01 mbar. After a small initial fraction (15 g with a boiling point up to 60° C./0.01 mbar), 401 g (2.36 moles, corresponding to a yield of 96%) of 2-tert-butyl-4-methylcyclohexanol distilled over at 80°-85° C./0.01 mbar and, after cooling, solidified to a semisolid mass. On the basis of 13C NMR spectroscopic data, the product was identified as a diastereomer mixture of the following composition: A:B:C:D=68:29:2:1 ##STR7##

Workup

  1. customwas initially taken in an autoclave and hydrogenated at 120° C. and under a hydrogen
  2. custom(total hydrogenation time about 3 1/2 hours)
  3. customThe catalyst was separated off
  4. distillationafter which the dioxane was distilled off
  5. distillationAfter a small initial fraction (15 g with a boiling point up to 60° C./0.01 mbar), 401 g (2.36 moles, corresponding to a yield of 96%) of 2-tert-butyl-4-methylcyclohexanol distilled over at 80°-85° C./0.01 mbar
  6. temperatureafter cooling, solidified to a semisolid mass
  7. additionOn the basis of 13C NMR spectroscopic data, the product was identified as a diastereomer mixture of the following composition

Sources & evidence

ORD record
ord-d0c542d7cf8a4e738d615d61cf99504f
Source dataset
uspto-grants-1988_07
Patent number
US04757051

Reaction notes

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