Methyl 5-methyl-3-oxohexanoate → Methyl 5-methyl-2-nitro-3-oxohexanoate

HRID 1427363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427363
[N:1]([O-:3])=[O:2].[Na+].[CH3:5][CH:6]([CH3:15])[CH2:7][C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11]>O.C(O)(=O)C>[CH3:5][CH:6]([CH3:15])[CH2:7][C:8](=[O:14])[CH:9]([N+:1]([O-:3])=[O:2])[C:10]([O:12][CH3:13])=[O:11]

Komponenten

5

Edukt 2

HCID 121701Methyl 5-methyl-3-oxohexanoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 42609287Methyl 5-methyl-2-nitro-3-oxohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of sodium nitrite (232 g, 3.36 mol) in water (560 mL) was added drop-wise over 1.5 hours to a solution of methyl 5-methyl-3-oxohexanoate (400 g, 2.53 mol) in glacial acetic acid (510 mL) at 20 to 25° C. Stirring was continued at room temperature for 2 hours. Water (1.3 L) was added, and the reaction mixture was stirred for an additional 18 hours. The mixture was then extracted with ethyl acetate (3×2.5 L), and the combined organic layers were washed sequentially with water (2.5 L), with aqueous sodium bicarbonate solution (2.5 L), and with saturated aqueous sodium chloride solution (1.0 L). After drying over sodium sulfate, the organic extracts were concentrated in vacuo to afford the product as a yellow liquid, which was used directly in the next step. Yield: 456 g, 2.24 mol, 89%.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for an additional 18 hours
  2. extractionThe mixture was then extracted with ethyl acetate (3×2.5 L)
  3. washthe combined organic layers were washed sequentially with water (2.5 L), with aqueous sodium bicarbonate solution (2.5 L)
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe organic extracts were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f1f5ce66f8fc41eda4ac5ac72eb074c5
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933224B2

Notizen zur Reaktion

Wird geladen…