Nitric Acid → 5-Ethoxycarbonyloxy-2-nitrobenzoic acid

HRID 851347Notes

Reaction equation

HRID 851347 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:5])[CH3:2].S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>O>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:15]=[CH:14][C:13]([N+:21]([O-:23])=[O:22])=[C:9]([CH:8]=1)[C:10]([OH:12])=[O:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 205022753-[(Ethoxycarbonyl)oxy]benzoic acid

Product 1

HCID 205022675-Ethoxycarbonyloxy-2-nitrobenzoic acidYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Finely ground 3-ethoxycarbonyloxybenzoic acid (10.5 g) was added with stirring to concentrated sulphuric acid at 2°. A mixture of concentrated sulphuric acid (10 ml) and 70% nitric acid (4.5 g) was then added dropwise with stirring, keeping the temperature at 5° or below. When addition was complete, the solution was stirred for another 30 minutes and then poured into ice and water (200 ml). The white solid which separated was washed with water and taken up in chloroform. The solution was dried (MgSO4) and concentrated to yield 5-ethoxycarbonyloxy-2-nitrobenzoic acid (9.8 g) with a melting point of 126°-130°.

Workup

  1. additionwas then added dropwise
  2. customat 5° or below
  3. additionWhen addition
  4. stirringthe solution was stirred for another 30 minutes
  5. customThe white solid which separated
  6. washwas washed with water
  7. dry with materialThe solution was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-65043f82d2824c98bd1779c4e48a726c
Source dataset
uspto-grants-1983_05
Patent number
US04384135

Reaction notes

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