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

Temperatur

-15 °C

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 20 (M+H)+.

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

ORD-Eintrag

ord-ce88d113a2344aa88f4981eed8d2b581

Quelldatensatz

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06184361B2