Hydrogen Peroxide → 2-Ethylhexanoic Acid

HRID 1375933Notes

Reaction equation

HRID 1375933 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].[OH:10]O.O>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[C:4]([OH:10])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 77202-Ethylhexanol

Product 1

HCID 86972-Ethylhexanoic AcidYield 65%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-ethyl hexanol (8.7 mmol) in CH2Cl2 (10 ml), RuCl3H2O (0.014 mmol) and tetra butyl ammonium bromide (0.2 mmol) were added. The mixture was heated at 40° C. and 30% H2O2 (v/v) (3 ml) was added dropwise. After 1 hours the reaction was complete. Water is added, the organic phase was separated, dried over sodium sulphate and evaporated under reduced pressure to give the crude product of the title that was purified by flash chromatography (pure CH2Cl2) obtaining 0.8 g of the desired product. Yield 65%.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customto give the crude product of the title that
  5. customwas purified by flash chromatography (pure CH2Cl2)

Sources & evidence

ORD record
ord-28e604ab9dd048c5af931ee4b1fc6467
Source dataset
uspto-grants-2007_01
Patent number
US07169890B2

Reaction notes

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