Acetone → 4-Ethoxycyclohexan-1-one

HRID 511392

Reaktionsgleichung

Reaktionsgleichung von HRID 511392
[CH2:1]([O:3][CH:4]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1)[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(C)=O>O>[CH2:1]([O:3][CH:4]1[CH2:13][CH2:12][C:7](=[O:8])[CH2:6][CH2:5]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5673588-Ethoxy-1,4-dioxaspiro[4.5]decane2×

Produkt 1

HCID 5464704-Ethoxycyclohexan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 8-Ethoxy-1,4-dioxa-spiro[4.5]decane (Compound 166F, 2 gm, 10.7 mmol) and pyridinium p-toluene sulfonate (5.4 gm, 21.5 mmol) was taken up in a 1:1 mixture of acetone and water (150 mL) and stirred at 50° C. overnight. The acetone was subsequently removed under reduced pressure and the aqueous solution was extracted with ethyl acetate. The organic layer was washed with water, dried (Na2SO4), and evaporated to give the crude material which was used in the next step without further purification. Yield: 0.8 gm (53%). 1H NMR (CDCl3, 500 MHz): δ 1.24 (t, J=7.1 Hz, 3H), 1.95 (m, 2H), 2.05 (m, 2H), 2.24 (m, 2H), 2.6 (m, 2H), 3.6 (q, J=7.1 Hz 2H), 3.7 (m, 1H).

Aufarbeitung

  1. customThe acetone was subsequently removed under reduced pressure
  2. extractionthe aqueous solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c7cfa3ad87444a74aa346534eacbb44c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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