Water → 4,4-Dimethyl-1-hydroxypentan-2-one

HRID 1927644

Reaction equation

HRID 1927644 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=[CH2:5].[Mn]([O-])(=O)(=O)=[O:9].[K+].N([O-])=O.[Na+].S(=O)(=O)(O)O.[OH2:23]>CC(C)=O.C(O)(=O)C>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][C:4](=[O:9])[CH2:5][OH:23]

Participants

8

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 129844,4-Dimethylpent-1-eneHCID 516875Potassium PermanganateHCID 23668193Sodium Nitrite

Product 1

HCID 213356424,4-Dimethyl-1-hydroxypentan-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×

Procedure

To a mixture of 4,4-dimethyl-1-pentene (10 g), acetone (600 mL), water (140 mL) and acetic acid (13.5 mL) at rt was added a solution of potassium permanganate (22.3 g) in water (85 mL), followed by additional acetone (270 mL). After stirring for 40 min, sodium nitrite (11.7 g) was added, followed by dilute sulfuric acid (12%, 221 mL). The product was extracted with ether:hexanes (1:1), and the extracts were washed with saturated sodium bicarbonate and brine, dried (sodium sulfate) and concentrated. The resulting residue was purified on silica gel column (5-100% ether in hexanes) to give the title compound.

Workup

  1. extractionThe product was extracted with ether:hexanes (1:1)
  2. washthe extracts were washed with saturated sodium bicarbonate and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting residue was purified on silica gel column (5-100% ether in hexanes)

Sources & evidence

ORD record
ord-e415e82c687e48c1a78d0ec9848f2bdc
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Linked notes

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