Sulfuric Acid → cis-2-Benzamidocyclohexanol

HRID 1449844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449844
[C:1]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[OH-].[Na+].N[C@H]1CCCC[C@H]1O>O>[C:1]([NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 6542151cis-2-AminocyclohexanolHCID 11020385trans-2-Benzamido-cyclohexanol

Produkt 1

HCID 36688674cis-2-BenzamidocyclohexanolAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 24 g (11 mmol) of racemic trans-2-benzamidocyclohexanol and 12 g of 90% H2SO4 (110 mmol) was stirred at 75°-80° for 6 hours. After the addition of 22 mL of H2O, the mixture was heated under reflux for 15 hours. The mixture was cooled to room temperature and washed with 20 mL of methylene chloride. The acidic aqueous phase was separated, treated with 12.6 mL of 50% NaOH solution (240 mmol) at <40° C., 30mL of H2O was added and the mixture extracted with a total of 60 mL of methylene chloride at 30°-35° C. The combined extracts were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to provide crude product containing cis-2-aminocyclohexanol which was isolated and purified by flash chromatography on silica gel with ethyl acetate-hexane (1:1) to provide 792 mg of cis-2-benzamidocyclohexanol (33% of theory). Proton and C13NMR were consistent with the proposed structure.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. washwashed with 20 mL of methylene chloride
  4. customThe acidic aqueous phase was separated
  5. extractionthe mixture extracted with a total of 60 mL of methylene chloride at 30°-35° C
  6. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto provide crude product
  10. customwas isolated
  11. custompurified by flash chromatography on silica gel with ethyl acetate-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-21c735eb35d0454f820474e5e4e03c9e
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599985

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