Thionyl Chloride → [1-(Chlorocarbonyl)cyclobutyl]methyl acetate

HRID 728695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728695
S(Cl)([Cl:3])=O.[C:5]([O:8][CH2:9][C:10]1([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11]1)(=[O:7])[CH3:6]>>[C:5]([O:8][CH2:9][C:10]1([C:14]([Cl:3])=[O:16])[CH2:13][CH2:12][CH2:11]1)(=[O:7])[CH3:6]

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 156705071-Acetoxymethylcyclobutanecarboxylic Acid

Produkt 1

HCID 15632048[1-(Chlorocarbonyl)cyclobutyl]methyl acetate

Versuchsvorschrift

Thionyl chloride (1.65 ml, 22.7 mmol) was added to neat 1-acetoxymethylcyclobutanecarboxylic acid (3.3 g, 18.9 mmol). The resulting mixture was stirred at room temperature for 1 hour, then heated on a steam bath for 5 minutes. After cooling, the excess thionyl chloride, HCl and SO2 were removed under reduced pressure (water aspirator). The remained residue was purified by distillation to provide the desired product as a colorless oil: bp 51-3° C. (0.02 mm); NMR (CDCl3) δ=1.8~2.7 (9H, m containing a singlet at 2.04 δ), 4.40 (2H, s).

Aufarbeitung

  1. temperatureheated on a steam bath for 5 minutes
  2. temperatureAfter cooling
  3. customthe excess thionyl chloride, HCl and SO2 were removed under reduced pressure (water aspirator)
  4. distillationThe remained residue was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-e17bfd1981d24aa486e8242cf92533ab
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05049696

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