Acetone → HCID 57591432, compound

HRID 1784123Notes

Reaction equation

HRID 1784123 reaction equation
[CH3:1][CH:2]([CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[O:8].[BH4-].[Na+].CC(C)=O>C(O)C>[CH3:1][CH:2]([CH:9]=[C:10]([CH3:11])[CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 575914337-Nonenal, 6,8-dimethyl-

Product 1

HCID 57591432HCID 57591432, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

18 g (0.11 mol) of 6,8-dimethylnon-7-enal (1) and 96.0 g of ethanol are placed in a 500 ml round-bottomed flask equipped with a thermometer. Cooling is carried out to 5° C. and 2.0 g of sodium borohydride are added in small portions without exceeding a bulk temperature of 10° C. The mixture is stirred at ambient temperature for 16 hours. Cooling is carried out to 5° C. and 20.0 g (1.36 mol) of acetone are added dropwise to destroy the excess reducing agent without exceeding a bulk temperature of 10° C. The reaction medium is acidified with 20.0 g of 10% hydrochloric acid without exceeding a bulk temperature of 10° C. 40 g of water are also added, followed by 70 g of toluene, with vigorous stirring. The phases are separated and the organic phase is washed once with 50 g of saturated aqueous NaHCO3 solution and twice with 50 g of water. The organic phase is dried and filtered, and the toluene is evaporated at reduced pressure. After distillation, 13.4 g (0.08 mol) of (B.p.: 105° C./10 torr) are obtained. The yield is 72.7%. The analyses of the infrared, NMR and mass spectra correspond to the expected alcohol.

Workup

  1. customequipped with a thermometer
  2. temperatureCooling
  3. customis carried out to 5° C.
  4. customa bulk temperature of 10° C
  5. temperatureCooling
  6. customis carried out to 5° C.
  7. customto destroy the
  8. customa bulk temperature of 10° C
  9. customa bulk temperature of 10° C
  10. addition40 g of water are also added
  11. customThe phases are separated
  12. washthe organic phase is washed once with 50 g of saturated aqueous NaHCO3 solution and twice with 50 g of water
  13. customThe organic phase is dried
  14. filtrationfiltered
  15. customthe toluene is evaporated at reduced pressure
  16. distillationAfter distillation, 13.4 g (0.08 mol) of (B.p.: 105° C./10 torr)
  17. customare obtained

Sources & evidence

ORD record
ord-9d5f7e23615a49bb80c50ab907f1f4fa
Source dataset
uspto-grants-2009_03
Patent number
US07501536B2

Reaction notes

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