Hydrochloric Acid → 1-((2-Benzoylphenylthio)methyl)cyclohexanecarboxaldehyde

HRID 2229508

Reaktionsgleichung

Reaktionsgleichung von HRID 2229508
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].S([O:20][CH2:21][C:22]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(C)(=O)=O.C(N(CC)CC)C.Cl>COCCOCCOC>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[S:1][CH2:28][C:22]1([CH:21]=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 34997132-MercaptobenzophenoneHCID 223252611-(Mesyloxymethyl)cyclohexanecarboxaldehyde

Produkt 1

HCID 223252081-((2-Benzoylphenylthio)methyl)cyclohexanecarboxaldehydeAusbeute 75,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

A mixture of 69 g (0.303 mole) of 2-mercaptobenzophenone, 82 g (0.303 mole) of mesylate 55, 32 g of triethylamine, and 150 ml of diglyme was stirred and held at reflux for 24 h. The mixture was cooled, poured into dil. HCl and extracted with methylene chloride. The organic layer was washed with 10% NaOH, water, brine, and dried over sodium sulfate and concentrated under vacuum to remove excess diglyme. This was purified by silica gel flush column (5% EtOAc:Hexane) and gave 18.6 g (75.9%) of yellow oil. Proton NMR and mass spectra were consistent with the product.

Aufarbeitung

  1. temperatureat reflux for 24 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with 10% NaOH, water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto remove excess diglyme
  8. customThis was purified by silica gel
  9. customflush column (5% EtOAc:Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2f71fdaa36f94a28b4301990659889dc
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420417B1

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