Hydrochloric Acid → 4-Oxo-2-adamantyl chloromethyl ether

HRID 2378516

Reaktionsgleichung

Reaktionsgleichung von HRID 2378516
[ClH:1].[O:2]=[C:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH:5]3[OH:13])[CH2:9]2.[CH2:14]=O.S([O-])([O-])(=O)=O.[Mg+2].[Cl-].[Na+].S(=O)(=O)(O)O>ClCCl>[Cl:1][CH2:14][O:2][CH:3]1[CH:4]2[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]1[CH2:9]3)[C:5]2=[O:13]

Komponenten

8

Edukt 6

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5334354-Hydroxyadamantan-2-one

Produkt 1

HCID 231508604-Oxo-2-adamantyl chloromethyl etherAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A separable flask having a volume of one liter equipped with a nozzle for introducing hydrogen chloride gas was equipped with a stirring device and charged with 50.0 g (301 mmol) of 4-oxo-2-adamantanol, 13.6 g (450 mmol) of paraformaldehyde, 36.2 g (300 mmol) of magnesium sulfate and 650 ml of dried dichloromethane, and it was cooled to 0° C. on an ice bath and stirred. Hydrogen chloride gas generated by mixing 300.7 g (5 mole) of sodium chloride with 700 ml of conc. sulfuric acid was blown thereinto through the nozzle for one hour. After further stirring for 3 hours, magnesium sulfate was filtered, and then the solution was analyzed by gas chromatography to confirm that 4-oxo-2-adamantanol was completely converted and that the intended product was obtained at a selectivity of 93.2%. Hydrogen chloride and dichloromethane were removed, and then refining was carried out by distillation to isolate 55.0 g (256 mmol, yield 85.2%, GC purity 98.8%) of the intended product.

Aufarbeitung

  1. customA separable flask having
  2. customa volume of one liter equipped with a nozzle
  3. customwas equipped with a stirring device
  4. stirringAfter further stirring for 3 hours
  5. filtrationmagnesium sulfate was filtered
  6. customwas obtained at a selectivity of 93.2%
  7. customHydrogen chloride and dichloromethane were removed
  8. distillationrefining was carried out by distillation
  9. customto isolate 55.0 g (256 mmol, yield 85.2%, GC purity 98.8%) of the intended product

Quellen und Nachweise

ORD-Eintrag
ord-bcaf0f06179d499eaa99df8ef268a52b
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470824B2

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