Acetone → 4-Hydroxy-4-methylcyclohexanone

HRID 1487615

Reaktionsgleichung

Reaktionsgleichung von HRID 1487615
[CH3:1][C:2]1([OH:12])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.CC(C)=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[OH:12][C:2]1([CH3:1])[CH2:11][CH2:10][C:5](=[O:6])[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 187130758-Methyl-1,4-dioxaspiro(4.5)decan-8-ol

Produkt 1

HCID 285394-Hydroxy-4-methylcyclohexanoneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 8-methyl-1,4-dioxaspiro[4.5]decan-8-ol (1 equiv) in a 2:1 mixture of acetone and water (0.38 M) was added pyridinium p-toluenesulfonate (0.2 equiv). The resulting mixture was refluxed for 8 h. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-30% ethyl acetate in petroleum ether) to afford the title compound (86% yield) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 3.96-3.93 (m, 2H), 2.27-2.25 (m, 1H), 2.25-2.22 (m, 1H), 2.01-1.94 (m, 2H), 1.90-1.82 (m, 2H), 1.38 (s, 3H).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 8 h
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (0-30% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-b36d079ecd774d149cc24c9f0936d772
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428509B2

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