4-tert-Butylphenol → 4-tert-Butylcyclohexanol

HRID 372919Notes

Reaction equation

HRID 372919 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C1CCCCC1>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([OH:11])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 73934-tert-ButylphenolHCID 178418361HCID 178418361, compound

Product 1

HCID 73914-tert-ButylcyclohexanolYield 98%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture consisting of 50 g (0.33 mole) of 4-tert-butyl-phenol, 1.35 g of the catalyst prepared as described above under example 1A and 100 g of cyclohexane was introduced in an autoclave under nitrogen and then hydrogen was introduced until a stable pressure around 16×105Pa had been established. The reaction mixture was then heated to about 98° and the reaction was followed by gas chromatography. After 135 min, the reaction was interrupted by cooling to around 45° and the autoclave was purged with a nitrogen flow. After filtering, the catalyst was recovered under a flow of argon, washed with cyclohexane and recycled for the following hydrogenation operations. 4-tert-Butyl-cyclohexanol was obtained by distillation of the clear filtrate in 98% yield. The isomeric content was 81.9% of the cis isomer and 15.9% of the trans isomer.

Workup

  1. customprepared
  2. additionwas introduced in an autoclave under nitrogen
  3. temperatureThe reaction mixture was then heated to about 98°
  4. temperatureby cooling to around 45°
  5. customthe autoclave was purged with a nitrogen flow
  6. filtrationAfter filtering
  7. customthe catalyst was recovered under a flow of argon
  8. washwashed with cyclohexane and recycled for the following hydrogenation operations

Sources & evidence

ORD record
ord-3ab203bbc9844b5cb6afffa1116b5881
Source dataset
uspto-grants-1992_11
Patent number
US05160498

Reaction notes

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