Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-(4-Hydroxymethylphenyl)cyclohexanone

HRID 1468769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468769
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:25][CH2:24][C:19]3(OCC[O:20]3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)(C)C)(C)(C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[OH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]2)=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68160088HCID 68160088, Verbindung

Produkt 1

HCID 193813914-(4-Hydroxymethylphenyl)cyclohexanoneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl-[4-(1,4-dioxa-spiro[4.5]dec-8-yl)benzyloxy]dimethylsilane (12.1 g, 33.3 mmol) in acetone (12 ml) and water (1.2 ml) was added pyridinium p-toluenesulfonate (2.51 g, 9.99 mmol) at room temperature. The mixture was refluxed for 3 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40) to afford 4-(4-hydroxymethylphenyl)cyclohexanone as a colorless solid (4.21 g, 20.6 mmol, 62%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40)

Quellen und Nachweise

ORD-Eintrag
ord-94209a6fbf184fb3a7b26c6517f76eac
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006232B2

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