Methyl iodide → Methyl 2-methyl-6-nitrobenzoate

HRID 133103

Reaktionsgleichung

Reaktionsgleichung von HRID 133103
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 160976-Methyl-2-nitrobenzoic acid

Produkt 1

HCID 596057Methyl 2-methyl-6-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of the 2-methyl-6-nitro-benzoic acid (5.6 g, 30.9 mmol, 1.0 eq, Aldrich) and acetone (100 mL) was added crushed K2CO3 (21.4 g, 154.6 mmol, 5 eq) and MeI (9.6 mL, 154.6 mmol, 5.0 eq.). The reaction was heated to reflux for 15 h then cooled to RT, filtered and concentrated in vacuo. The filtrate was dissolved in EtOAc, washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give the desired compound as a reddish-brown oil which upon standing at RT crystallized as tan needles.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe filtrate was dissolved in EtOAc
  6. washwashed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ca3edb7fbf8848eeaa728149acea2bb2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390820B2

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