Water → 1-Cyclohexyl-3-hydroxyacetone

HRID 425332Notes

Reaction equation

HRID 425332 reaction equation
[CH:1]1([CH2:7][CH:8]=[CH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Mn]([O-])(=O)(=O)=[O:11].[K+].N([O-])=O.[Na+].S(=O)(=O)(O)O.[OH2:25]>CC(C)=O.C(O)(=O)C>[CH:1]1([CH2:7][C:8](=[O:11])[CH2:9][OH:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 75027AllylcyclohexaneHCID 516875Potassium PermanganateHCID 23668193Sodium Nitrite

Product 1

HCID 124315481-Cyclohexyl-3-hydroxyacetone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent2×

Procedure

To a mixture of 3-cyclohexyl-1-propene (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 eluting with 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
  6. washeluting with 5-100% ether in hexanes

Sources & evidence

ORD record
ord-61b19f20473c4b14afadec595f826c54
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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