Ethyl Acetate → 2,2,5,5-Tetramethylcyclopentan-1-ol

HRID 35435Notes

Reaction equation

HRID 35435 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3]1=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1382872,2,5,5,-TetramethylcyclopentanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 5516962,2,5,5-Tetramethylcyclopentan-1-olYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred solution of 10 g (0.071 mol) 2,2,5,5-tetramethylcyclopentanone in 75 ml of dry tetrahydrofuran at 0° C. under argon is added 2.69 g (0.071 mol) of lithium aluminum hydride. When the reduction was complete, ethyl acetate was introduced dropwise to destroy unreacted lithium aluminum hydride. 25 mls of water is then added, followed by 300 mls of diethyl ether. The organic phase is washed with 100 mls of water, and dried over MgSO4. Filtration followed by evaporation afforded 8.23 g of 2,2,5,5-tetramethylcyclopentanol.

Workup

  1. customto destroy unreacted lithium aluminum hydride
  2. addition25 mls of water is then added
  3. washThe organic phase is washed with 100 mls of water
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-bdca90d81c604ce08ab4d87250b6bdb7
Source dataset
uspto-grants-1988_08
Patent number
US04766246

Reaction notes

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