3,4-Dihydroxy-5-nitrobenzoic acid → 3,4-Diacetoxy-5-nitrobenzoic acid

HRID 274514Notes

Reaction equation

HRID 274514 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6]>C(OC(=O)C)(=O)C>[C:2]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[O:11][C:5](=[O:6])[CH3:4])[C:5]([OH:7])=[O:6])(=[O:1])[CH3:10]

Participants

3

Reactant 1

HCID 144509823,4-Dihydroxy-5-nitrobenzoic acid

Product 1

HCID 154807403,4-Diacetoxy-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

7.3 g of 3,4-dihydroxy-5-nitrobenzoic acid are treated with 30 ml of acetic anhydride, whereupon the mixture is held at the reflux temperature for 8 hours. The reaction mixture is poured on to ice. The separated precipitate is filtered under suction, washed with water and taken up in methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The residue obtained is recrystallized from methylene chloride/n-hexane in the cold. There is obtained 3,4-diacetoxy-5-nitrobenzoic acid in the form of colorless crystals of m.p. 126°-127°.

Workup

  1. additionThe reaction mixture is poured on to ice
  2. filtrationThe separated precipitate is filtered under suction
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis recrystallized from methylene chloride/n-hexane in the cold

Sources & evidence

ORD record
ord-f17f190c97b74fadbd38a43487a49f6c
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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