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p-Toluenesulfonic acid monohydrate → 4-Methoxy-4-(trifluoromethyl)cyclohexan-1-one

HRID 922120
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922120
[CH3:1][O:2][C:3]1([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[CH3:1][O:2][C:3]1([C:13]([F:14])([F:15])[F:16])[CH2:4][CH2:5][C:6](=[O:7])[CH2:11][CH2:12]1
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Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 712468178-Methoxy-8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane

Produkt 1

HCID 894014664-Methoxy-4-(trifluoromethyl)cyclohexan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

11.80 g (49.12 mmol) of 8-methoxy-8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane (Example 9A) were dissolved in 236 ml of acetone and 118 ml of water, 1.50 g (7.86 mmol) of 4-toluenesulphonic acid monohydrate were added and the mixture was heated at reflux overnight. The mixture was then poured into 1.2 l of water and the product was extracted with diethyl ether. The organic phase was washed with water, dried over sodium sulphate and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (boiling point: 106-110° C. at 40 mbar). This gave 6.86 g (71% of theory) of the title compound as a yellowish oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. extractionthe product was extracted with diethyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. distillationThe resulting residue was distilled under reduced pressure (boiling point: 106-110° C. at 40 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-85c9c50769a94a8da60ee05842c2430a
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278925B2

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