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

HRID 620681Notes

Reaction equation

HRID 620681 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-tetramethycyclopentanone 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 into 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 into 100 mls of water
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-9d795d4122e94ff1b813158727a7e4f1
Source dataset
uspto-grants-1989_04
Patent number
US04822635

Reaction notes

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