Water → 1-Cyclohexyl-3-hydroxyacetone

HRID 1881410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881410
[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

Komponenten

8

Edukt 5

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

Produkt 1

HCID 124315481-Cyclohexyl-3-hydroxyacetone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70cd60aac10d44b1b277bf5ea0e3834c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318767B2

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