Hydrochloric Acid → 2,4-DI-Tert-butylcyclohexanol

HRID 277317Notes

Reaction equation

HRID 277317 reaction equation
[C:1]([CH:5]1[CH2:10][CH:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:8][CH2:7][C:6]1=[O:15])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC>[C:1]([CH:5]1[CH2:10][CH:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:8][CH2:7][CH:6]1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 114442Cyclohexanone, 2,4-bis(1,1-dimethylethyl)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 5460322,4-DI-Tert-butylcyclohexanolYield 88.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
23 °C

Procedure

380 g of 2,4-di-tert-butylcyclohexanone (mixed isomers) in 200 ml of ether are added dropwise with vigorous stirring to a suspension of 34.3 g (903 mmol) of lithium aluminium hydride in 1800 ml of ether over 4 hours, and the batch is subsequently stirred at 23° C. for 1 hour and admixed with 500 ml of 5% hydrochloric acid by vigorous stirring. The organic phase is separated off and washed twice with 250 ml of water each time. The organic phase is dried over MgSO4, evaporated and dried under reduced pressure to leave 337.80 g (88% of theory) of 2,4-di-tert-butylcyclohexanol (mixed isomers) as colourless wax.

Workup

  1. customThe organic phase is separated off
  2. washwashed twice with 250 ml of water each time
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8f6d695d03b5483caacc35b13a61e400
Source dataset
uspto-grants-2002_03
Patent number
US06355783B1

Reaction notes

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