Methanol → Methyl 2-methyl-4-nitrobenzoate

HRID 1039085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039085
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:19]O>>[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:19])=[O:10]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 747904-Nitro-o-toluic acid

Produkt 1

HCID 15088700Methyl 2-methyl-4-nitrobenzoate

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Sulfuric acid (6 ml, 113 mmol) was added to drop wise to a solution of the 2-methyl-4-nitrobenzoic acid (5 g, 27.6 mmol) in MeOH (138 ml) at RT. After the addition was complete the mixture was heated to 55° C. overnight. The volatiles were removed in vacuum and the residue partitioned between EtOAc (100 ml) and water (100 ml). The layers were separated and aqueous phase extracted with EtOAc (2×100 ml). The organic fractions were combined, washed with saturated sodium bicarbonate (aqueous, 100 ml), brine, dried over Na2SO4, filtered and the volatiles removed in vacuum to give the titled compound.

Aufarbeitung

  1. additionAfter the addition
  2. customThe volatiles were removed in vacuum
  3. customthe residue partitioned between EtOAc (100 ml) and water (100 ml)
  4. customThe layers were separated
  5. extractionaqueous phase extracted with EtOAc (2×100 ml)
  6. washwashed with saturated sodium bicarbonate (aqueous, 100 ml), brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe volatiles removed in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e45486ce10b94518a167680bb201e019
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552022B2

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