Water → HCID 86675568, compound

HRID 2405669Notes

Reaction equation

HRID 2405669 reaction equation
[CH2:1]([CH:5]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:6](=[O:8])[CH3:7])[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:1]([CH:5]([CH2:9][CH2:10][CH:11]([CH3:12])[CH3:13])[CH:6]([OH:8])[CH3:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86675569HCID 86675569, compound

Product 1

HCID 86675568HCID 86675568, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

3-butyl-6-methylheptan-2-one (5.00 g, 27.1 mmol) was dissolved in dry THF (70 ml). The solution was cooled to −15° C., and a suspension of LiAlH4 (3.5M, 2.7 ml, 9.45 mmol) was added over 15 minutes under stirring. After one hour at −15° C., a complete conversion was observed. The grey suspension was warmed to 0° C., and hydrolyzed by slow and successive addition of: water (0.36 g), 15% aqueous NaOH (0.36 g) and water (1.08 g). After warming to room temperature, the white precipitate was filtered, and the solvent removed under vacuum. The crude product was distilled bulb-to-bulb (Kugelrohr, oven 50° C., 0.2 mbar) (yield: 74.5%).

Workup

  1. additionwas added over 15 minutes
  2. temperatureThe grey suspension was warmed to 0° C.
  3. temperatureAfter warming to room temperature
  4. filtrationthe white precipitate was filtered
  5. customthe solvent removed under vacuum
  6. distillationThe crude product was distilled bulb-to-bulb (Kugelrohr, oven 50° C., 0.2 mbar) (yield: 74.5%)

Sources & evidence

ORD record
ord-ac28e1cdf08a422ea9d2558a55f50360
Source dataset
uspto-grants-2014_08
Patent number
US08809256B2

Reaction notes

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