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

HRID 2243483Notes

Reaction equation

HRID 2243483 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d0bfc028436f4383942956f772502599
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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