Hydrochloric Acid → 3-Oxaspiro(5,5)undecan-2-one

HRID 2223834Notes

Reaction equation

HRID 2223834 reaction equation
[C:1]12([CH2:12][C:11](=O)[O:10][C:8](=[O:9])[CH2:7]1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.[BH4-].[Na+].O.Cl>C1COCC1>[CH2:7]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:12][CH2:11][O:10][C:8]1=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27342891,1-Cyclohexanediacetic AnhydrideHCID 4311764Sodium borohydride

Product 1

HCID 224123-Oxaspiro(5,5)undecan-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-cyclohexane diacetic acid anhydride (20.1 g) in THF (150 mL) was added sodium borohydride (3.78 g, 100 mmol) under ice cooling. The reaction solution was stirred at room temperature for additional 3 hours. Water was added to the solution, and it was made acidic with conc. hydrochloric acid. The solution was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated under reduced pressure to give the title compound (17.07 g). This product was subjected to the subsequent step without further purification.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-26212eec4fd04965a6de55f9b3e63209
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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