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

HRID 2294899Notes

Reaction equation

HRID 2294899 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)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.C(O)C>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]2)[O:11][CH2:1]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-olYield 88.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,4-cyclohexanedione monoethylene ketal (3.12 g, 20 mmol) in dioxane (25 mL) and ethanol (45 mL) was added NaBH4 (0.38 g, 10 mmol) and the resulting mixture was refluxed for 45 min. The mixture was then cooled to room temperature, acidified to pH 5 with 10% citric acid and extracted with ethyl acetate to afford crude 1-hydroxy-4-cyclohexanone ethylene ketal (2.8 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 45 min
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-7e925f92675d45fcbc2d96836660e995
Source dataset
uspto-grants-1997_11
Patent number
US05691351

Reaction notes

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