Sulfuric Acid → Chromic Acid

HRID 2118570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118570
[O-2:1].[O-2:2].[O-2:3].[Cr+6:4].S(=O)(=O)(O)[OH:6].[CH:10]1([CH:16]([OH:19])[C:17]#[CH:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O.CC(C)=O>[Cr:4]([OH:6])([OH:3])(=[O:2])=[O:1].[CH:10]1([C:16](=[O:19])[C:17]#[CH:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

7

Edukt 3

HCID 1118Sulfuric AcidHCID 199445alpha-EthynylcyclohexanemethanolHCID 10219390chromium (VI) trioxide

Produkt 2

HCID 24425Chromic AcidHCID 103517531-Cyclohexyl-2-propyn-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of chromic acid was prepared by dissolving 106.88 g chromium trioxide in 400 ml water and then adding 92 ml concentrated sulfuric acid. This solution was added in dropwise fashion over a 3 hour period to an ice cooled, stirred solution of 120 g 3-cyclohexyl-1-propyn-3-ol in 175 ml acetone. The resulting mixture was diluted with 500 ml water and the product was extracted into 1 liter of diethyl ether. The ether extract was washed with 250 ml saturated sodium bisulfite solution and was dried over sodium sulfate. The diethyl ether was removed by distillation under nitrogen atmosphere and the resulting residue was purified by Kugelrohr distillation (65° C., 0.1 mm Hg) to give 84.9 g of 3-cyclohexyl-1-propyn-3-one as an oil: MS m/z=136 (M+) Calcd. for C9H12O: C, 79.37; H, 8.88. Found: C, 79.24; H, 8.6.

Aufarbeitung

  1. temperaturecooled
  2. extractionthe product was extracted into 1 liter of diethyl ether
  3. extractionThe ether extract
  4. washwas washed with 250 ml saturated sodium bisulfite solution
  5. dry with materialwas dried over sodium sulfate
  6. customThe diethyl ether was removed by distillation under nitrogen atmosphere
  7. distillationthe resulting residue was purified by Kugelrohr distillation (65° C., 0.1 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-b1936fcafcfb45cfa9956941f442759a
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04678805

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