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

HRID 234641Notes

Reaction equation

HRID 234641 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-72d7a6ead16d4f26b2efff5b071f7349
Source dataset
uspto-grants-1997_01
Patent number
US05595992

Reaction notes

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