1,4-Dioxaspiro(4.5)decane → 2-(Cyclohexyloxy)ethanol

HRID 2200578Notes

Reaction equation

HRID 2200578 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1>C1COCC1.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[CH:7]1([O:3][CH2:4][CH2:5][OH:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 90931,4-Dioxaspiro(4.5)decaneHCID 4311764Sodium borohydride

Product 1

HCID 2247752-(Cyclohexyloxy)ethanolYield 59.2%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To the slurry of zirconium tetrachloride (10.65 g, 45.7 mmol) in THF (100 mL) was added sodium borohydride (4.3 g, 114.3 mmol) in small portions at room temperature. A solution of 1,4-dioxaspiro[4.5]decane (6.5 g, 45.7 mmol) in THF (20 mL) was added dropwise and the resulting mixture was stirred at room temperature overnight. The reaction was carefully quenched with 1N HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried and concentrated to give a crude product, which was purified via silica gel chromatography eluting with petroleum ether/ethyl acetate (3:2) to give 2-(cyclohexyloxy)ethanol (3.9 g, 59.2% yield) as light yellow oil. 1H-NMR (CDCl3) δ 3.68-3.70 (t, 2H), 3.53-3.56 (m, 2H), 3.27-3.29 (m, 1H), 2.54 (br, 1H), 1.89-1.93 (m, 2H), 1.70-1.73 (m, 2H), 1.51-1.54 (m, 1H), 1.17-1.28 (m, 5H).

Workup

  1. customThe reaction was carefully quenched with 1N HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas purified via silica gel chromatography
  8. washeluting with petroleum ether/ethyl acetate (3:2)

Sources & evidence

ORD record
ord-a0bfe289eb574ddda337dc453c8d3f1a
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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