Sulfuric Acid → 1,3-di-tert-Butyl 5-nitrobenzene-1,3-dicarboxylate

HRID 581170Notes

Reaction equation

HRID 581170 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:21][C:22](=[CH2:24])[CH3:23]>ClCCl>[C:22]([O:10][C:9]([C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:13]([O:15][C:6]([CH3:13])([CH3:7])[CH3:5])=[O:14])[CH:7]=1)=[O:11])([CH3:23])([CH3:21])[CH3:24]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 120695-Nitroisophthalic acid

Product 1

HCID 540121621,3-di-tert-Butyl 5-nitrobenzene-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Nitroisophthalic acid (4.22 g, 20 mmol) was suspended in dichloromethane (80 ml) and concentrated sulphuric acid (1 ml) was added. The solution was stirred and then saturated with isobutylene gas. The reaction vessel was stoppered and stirred at room temperature overnight. The solution was filtered and anhydrous potassium carbonate was added to the filtrate. the solution was filtered and evsaporated and the residue recrystallised from ethanol to leave the title compound as a white solid (2.2 g).

Workup

  1. stirringstirred at room temperature overnight
  2. filtrationThe solution was filtered
  3. additionanhydrous potassium carbonate was added to the filtrate
  4. filtrationthe solution was filtered
  5. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-5753f5aef7c3445caa610b07a58cadb6
Source dataset
uspto-grants-1999_07
Patent number
US05919829

Reaction notes

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