Hydrochloric Acid → Methyl 5-chloro-4-nitroso-5-methylhexanoate

HRID 278382

Reaktionsgleichung

Reaktionsgleichung von HRID 278382
[N:1]([O:3]CCC(C)C)=O.[CH3:9][C:10]([CH3:18])=[CH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].[ClH:19]>>[Cl:19][C:10]([CH3:18])([CH3:9])[CH:11]([N:1]=[O:3])[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 10909672Methyl 5-methyl-4-hexenoate

Produkt 1

HCID 10058870Methyl 5-chloro-4-nitroso-5-methylhexanoate

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A mixture of isoamyl nitrite (12 mL) and methyl 5-methyl-4-hexenoate (4.90 g, 35.00 mmol) was cooled to −15° C. To this stirred solution, concentrated HCl (12.5 mL) was added dropwise from an addition flask maintaining the temperature of the reaction mixture below −5° C. After the addition, the reaction mixture was stirred at 0° C. for 30 minutes, filtered and the precipitate washed with ethanol (−10° C.). The light blue colored solid thus obtained was dispersed in petroleum ether (50 mL), cooled to ˜−50° C. and filtered to provide the title product as a colorless solid. Yield: 3.0 g (41.3%); m.p. 90-91° C. 1H NMR (CDCl3) δ 1.68 & 1.71 [2s, 6H, C(CH3)2], 2.35 [m, 4H, (CH2)2], 3.73 (s, 3H, COOCH3) and 5.11 (t, 1H, CH). MS m/e 208 (M+H)+.

Aufarbeitung

  1. temperaturemaintaining the temperature of the reaction mixture below −5° C
  2. additionAfter the addition
  3. filtrationfiltered
  4. washthe precipitate washed with ethanol (−10° C.)
  5. customThe light blue colored solid thus obtained
  6. temperaturecooled to ˜−50° C.
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c05a43d8fa9d417bafafee0da18c7c84
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359120B1

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