Acetone → Nonane

HRID 1803655Notes

Reaction equation

HRID 1803655 reaction equation
OC[C:3]([CH3:7])([CH2:5]O)C.[CH3:8][C:9]([CH3:11])=O.[CH3:12][CH:13](O)[CH3:14]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:5][CH2:3][CH3:7]

Participants

5

Reactant 3

HCID 180AcetoneHCID 3776IsopropanolHCID 31344Neopentyl glycol

Product 1

HCID 8141NonaneYield 65%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A solution of (0 mmol) of 0, (0.12 mmol) of 12, 14 mg (0.13 mmol) of neopentyl glycol, 95 mg (0.3 mmol) of Ba(OH)2.8H2O, 80 μl (6.08 mmol, 5 mol %) of a 76 mM acetone solution of Pd(OAc)2 in 2 ml of 95% i-PrOH is stirred at 80° C. for 12 hours. The solvent is subsequently removed under reduced pressure, 2 ml of 2 M HCl are added to the residue, and the mixture is extracted with dichloromethane (3×2 ml). The combined organic phases are dried over MgSO4 and filtered through SiO2. The solvent is removed under reduced pressure, and the residue is purified by recrystallisation ice from nonane (yield: 65%).

Workup

  1. customThe solvent is subsequently removed under reduced pressure, 2 ml of 2 M HCl
  2. additionare added to the residue
  3. extractionthe mixture is extracted with dichloromethane (3×2 ml)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered through SiO2
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-99b4d973ebc44ed1ab9ed689a7ae99dc
Source dataset
uspto-grants-2013_01
Patent number
US08350100B2

Reaction notes

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