1,4-Dioxaspiro[4.5]decan-8-one → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 582590Notes

Reaction equation

HRID 582590 reaction equation
[BH4-].[Na+].[CH2:3]1[O:13][C:6]2([CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)[O:5][CH2:4]1>CC(C)=O>[CH2:4]1[O:5][C:6]2([CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2)[O:13][CH2:3]1

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.6 g (95 mmol) of NaBH4 are added to a solution of 50 g (25 mmol) of 1,4-cyclohexanedione monoethylene ketal and the mixture is stirred until the reaction is complete. For working up, 30 ml of acetone are added and stirring is continued for 30 minutes. The mixture is subsequently evaporated to dryness and the residue is taken up in 200 ml of ether, the organic phase is washed with aqueous NH4Cl solution and water, and the organic phase is dried over MgSO4. The solvent is subsequently evaporated on a rotary evaporator and the residue is dried.

Workup

  1. stirringstirring
  2. customThe mixture is subsequently evaporated to dryness
  3. washthe organic phase is washed with aqueous NH4Cl solution and water
  4. dry with materialthe organic phase is dried over MgSO4
  5. customThe solvent is subsequently evaporated on a rotary evaporator
  6. customthe residue is dried

Sources & evidence

ORD record
ord-02303d41a2a940d79f8f19fb41909ab2
Source dataset
uspto-grants-1999_07
Patent number
US05925653

Reaction notes

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