2,2,5,5-tetramethyl cyclohexanone → 1,2,2,5,5-Pentamethylcyclohexan-1-ol

HRID 542905Notes

Reaction equation

HRID 542905 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]1=[O:10].[CH3:12][Li]>CCOCC>[CH3:12][C:3]1([OH:10])[CH2:4][C:5]([CH3:9])([CH3:8])[CH2:6][CH2:7][C:2]1([CH3:11])[CH3:1]

Participants

4

Reactant 2

HCID 148124172,2,5,5-tetramethyl cyclohexanoneHCID 178418348HCID 178418348, compound

Product 1

HCID 230492381,2,2,5,5-Pentamethylcyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 26.4 g of 2,2,5,5-tetramethylcyclohexanone in 250 ml of ether is added dropwise at -20° C. to 102.8 ml of methyl lithium (2 molar in ether). After stirring at 0° C. for 2.5 hours, the mixture is poured into ice/1N hydrochloric acid and extracted with ether. The organic phase is washed with water, dried and evaporated. The residue is distilled in a water-jet vacuum. There are obtained 22.6 g of 1,2,2,5,5-pentamethylcyclohexanol as a colorless liquid, b.p. 81°-87° C./17 mm.

Workup

  1. extractionextracted with ether
  2. washThe organic phase is washed with water
  3. customdried
  4. customevaporated
  5. distillationThe residue is distilled in a water-jet vacuum

Sources & evidence

ORD record
ord-10afe48742774fe28172c9006274ce56
Source dataset
uspto-grants-1987_04
Patent number
US04659735

Reaction notes

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