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

HRID 1735320Notes

Reaction equation

HRID 1735320 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 monoethylene 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-b307829a69a9433c986892422a452d1f
Source dataset
uspto-grants-1996_07
Patent number
US05536725

Reaction notes

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