Sulfuric Acid → Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoate

HRID 2243483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2243483
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:18]=[C:17]([C:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])([O-:8])=[O:7].[CH2:22]=[C:23]([CH3:25])[CH3:24]>O1CCOCC1.CCOC(C)=O>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:17]([C:19]([O:21][C:23]([CH3:25])([CH3:24])[CH3:22])=[O:20])=[CH:18][C:9]=1[N+:6]([O-:8])=[O:7]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 69956091,4-Benzenedicarboxylic acid, 2-nitro-, 1-methyl ester

Produkt 1

HCID 23291046Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sulfuric acid conc (5 ml) was added to a solution of 1-methyl 2-nitroterephthalate (25.2 g, 0.112 mmol) in dioxane (120 ml) in a Parr shaker bottle and cooled to 0° C. Isobutene (100 ml) was added, the vessel was sealed, and vigorously shaken for 5 days. The crude product was dissolved in EtOAc after evaporation of the excess isobutene and washed with sat NaHCO3. The organic layer was dried over MgSO4, filtered, and evaporated leaving 23.0 g (73%) of 2-nitroterephthalic acid 4-tert-butyl ester 1-methyl ester as a yellow liquid.

Aufarbeitung

  1. customthe vessel was sealed
  2. customafter evaporation of the excess isobutene
  3. washwashed
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d0bfc028436f4383942956f772502599
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674822B2

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