Hydrochloric Acid → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 2386946Notes

Reaction equation

HRID 2386946 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+].Cl.[Cl-].[Na+]>CO>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-olYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-dioxaspiro[4.5]decan-8-one (11.0 g, 6.40 mmol) was dissolved in methanol (10 mL), sodium borohydride (242 mg, 6.40 mmol) was slowly added, and stirred at room temperature for 5 minutes. The mixture was cooled on an ice bath, 10% hydrochloric acid aqueous solution and sodium chloride were added, and the mixture extracted with ethyl acetate. The organic phase was washed with saturated brine, and dried by anhydrous sodium sulfate. The sodium sulfate was filtered off, and the product concentrated under reduced pressure to obtain the target compound (614 mg, 61%) as a light yellow oily substance.

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic phase was washed with saturated brine
  4. dry with materialdried by anhydrous sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe product concentrated under reduced pressure

Sources & evidence

ORD record
ord-39a4e36441d74f44afddb4e27e8326b6
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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