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

HRID 727186Notes

Reaction equation

HRID 727186 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[O:3]1[C:4]2([CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]2)[O:11][CH2:1][CH2:2]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 702EthanolSolvent

Procedure

A solution of 15.6 grams (0.10 mole) of 1,4-cyclohexanedione mono-ethylene ketal in about 40 mL of ethanol is stirred, and 1.9 grams (0.05 mole) of sodium borohydride is added portionwise during a one hour period. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about four hours. After this time the reaction mixture is concentrated under reduced pressure to a residue. The residue is taken up in about 40 mL of water, and the mixture is extracted with three 25 mL portions of diethyl ether. The combined extracts are washed with an aqueous solution saturated with sodium chloride. The organic layer is then dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 1,4-dioxaspiro-[4.5]decan-8-ol

Workup

  1. additionUpon completion of addition
  2. concentrationAfter this time the reaction mixture is concentrated under reduced pressure to a residue
  3. extractionthe mixture is extracted with three 25 mL portions of diethyl ether
  4. washThe combined extracts are washed with an aqueous solution saturated with sodium chloride
  5. dry with materialThe organic layer is then dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-abbf331dd6b74203adec76c71a3973fe
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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