Hydrochloric Acid → 3-(cyclohexyloxy)propan-1-ol

HRID 422949Notes

Reaction equation

HRID 422949 reaction equation
[BH4-].[Na+].[CH2:3]1[O:13][C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.Cl>O1CCCC1.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[CH:7]1([O:6][CH2:5][CH2:4][CH2:3][OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 90961,5-Dioxaspiro(5.5)undecaneHCID 4311764Sodium borohydride

Product 1

HCID 100348783-(cyclohexyloxy)propan-1-olYield 78%

Reagents, catalysts & solvents 2

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

Procedure

Subsequently, to a suspension of zirconium chloride (24.9 g, 0.11 mol) in tetrahydrofuran (500 ml) was added slowly sodium borohydride (20.5 g, 0.54 mol) in portions with stirring under a nitrogen atmosphere, and the resulting mixture was stirred at room temperature for 20 minutes. After stirring, to the reaction mixture was added dropwise a solution of cyclohexanone trimethylene ketal (16.9 g, 0.11 mol) obtained above in tetrahydrofuran (170 ml) with stirring while ice-cooling under a nitrogen atmosphere, and then the resulting mixture was stirred at room temperature for one day. After stirring, to the reaction mixture was added ice-chilled 2N hydrochloric acid (600 ml) with stirring under ice-cooling to quench the reaction, and then the tetrahydrofuran was evaporated in vacuo. The aqueous layer which remained was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (10:1-5:2) as the eluent to afford 3-cyclohexyloxypropan-1-ol (13.4 g, yield: 78%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 20 minutes
  2. stirringAfter stirring, to the reaction mixture
  3. stirringwith stirring while ice-
  4. temperaturecooling under a nitrogen atmosphere
  5. stirringthe resulting mixture was stirred at room temperature for one day
  6. stirringAfter stirring, to the reaction mixture
  7. additionwas added ice-
  8. stirringwith stirring under ice-
  9. temperaturecooling
  10. customto quench
  11. customthe reaction
  12. customthe tetrahydrofuran was evaporated in vacuo
  13. extractionThe aqueous layer which remained was extracted with ethyl acetate
  14. washthe extract was washed with saturated aqueous sodium chloride solution
  15. dry with materialdried over anhydrous sodium sulfate
  16. filtrationAfter filtration
  17. customthe solvent was removed in vacuo
  18. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b82ef16a6d2c4f8d86f56aefe626d21d
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

Loading…