2,3-Dimethylphenol → HCID 13192288, Verbindung

HRID 2058974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2058974
[CH3:1][S:2]([N:5]1[CH2:11][CH2:10][CH:9]2[O:12][CH:8]2[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[OH:21].[OH-].[Na+]>C(#N)C>[OH:12][C@H:8]1[C@H:9]([O:21][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:14]=2[CH3:13])[CH2:10][CH2:11][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]1

Komponenten

5

Edukt 3

HCID 106872,3-DimethylphenolHCID 14798Sodium HydroxideHCID 205489081-methanesulphonyl-hexahydro-4,5-epoxy-1H-azepine

Produkt 1

HCID 13192288HCID 13192288, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

7.0 g (0.036 mol) of 1-methanesulphonyl-hexahydro-4,5-epoxy-1H-azepine are dissolved, together with 8.9 g (0.073 mol) of 2,3-dimethyl-phenol, with 36.6 ml of 2 N sodium hydroxide solution (0.013 mol) in 200 ml of acetonitrile. The reaction mixture is heated under reflux for 5 days, then cooled to room temperature and concentrated under a water pump vacuum. The residue is then dissolved in 200 ml of methylene chloride and the organic phase is washed with three times 100 ml of 2 N sodium hydroxide solution and then with water, dried over sodium sulphate and evaporated under a water pump vacuum. The resulting crude product is purified by preparative thick layer chromatography (100×20 cm silica gel plates, layer thickness 1.5 mm). Crystalline trans-4-hydroxy-5-(2,3-dimethylphenoxy)-1-methanesulphonyl-hexahydro-1H-azepine with a melting point of 112°-115° is obtained by elution with a 3:1 mixture of toluene/ethyl acetate.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 5 days
  3. concentrationconcentrated under a water pump vacuum
  4. dissolutionThe residue is then dissolved in 200 ml of methylene chloride
  5. washthe organic phase is washed with three times 100 ml of 2 N sodium hydroxide solution
  6. dry with materialwith water, dried over sodium sulphate
  7. customevaporated under a water pump vacuum
  8. customThe resulting crude product is purified by preparative thick layer chromatography (100×20 cm silica gel plates, layer thickness 1.5 mm)

Quellen und Nachweise

ORD-Eintrag
ord-7dcbefb13ab349adb2199ebd7a39a829
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04320137

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