4-tert-Butylcyclohexanone → 4-tert-Butylcyclohexanol

HRID 372920Notes

Reaction equation

HRID 372920 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]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 73924-tert-ButylcyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 73914-tert-ButylcyclohexanolYield 93.8%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture composed of 100 g (0.649 mole) of 4-tert-butyl-cyclohexanone, 1.35 g of the catalyst prepared as indicated in Example 1 and 150 g of cyclohexane were put into an autoclave under nitrogen and then hydrogen was introduced until the pressure settled at about 106Pa. The mixture was then heated to 70° and the reaction was followed by gas chromatography. The reaction was stopped by cooling and the autoclave was flushed with nitrogen. After filtering, the catalyst was recovered under argon flow, washed with cyclohexane and recycled for the following hydrogenation operations. The clear filtrate was evaporated to give a residue that, once distilled, provided 95.15 g of an isomeric mixture containing 87.7% of cis isomer.

Workup

  1. customprepared
  2. temperatureThe mixture was then heated to 70°
  3. temperatureby cooling
  4. customthe autoclave was flushed with nitrogen
  5. filtrationAfter filtering
  6. customthe catalyst was recovered under argon flow
  7. washwashed with cyclohexane and recycled for the following hydrogenation operations
  8. customThe clear filtrate was evaporated
  9. customto give a residue that
  10. distillationonce distilled

Sources & evidence

ORD record
ord-a383ce2d5c44418597869044400026c2
Source dataset
uspto-grants-1992_11
Patent number
US05160498

Reaction notes

Loading…