Nitric Acid → 5,6-Dihydroxy-7-nitro-2-benzofuran-1(3H)-one

HRID 1881157Notes

Reaction equation

HRID 1881157 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[O:6][CH2:5]2.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[OH:11])[C:7](=[O:12])[O:6][CH2:5]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 206222605,6-Dihydroxyisobenzofuran-1(3H)-one

Product 1

HCID 159828415,6-Dihydroxy-7-nitro-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 5,6-dihydroxy-3H-isobenzofuran-1-one (0.4 g) in sulfuric acid at −30° C. was added 5 M nitric acid in sulfuric acid (0.55 ml). The reaction mixture was let to warm up to room temperature and then poured into ice water. The product was filtered and recrystallized from acetic acid.

Workup

  1. filtrationThe product was filtered
  2. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-8ce25539c24c41c6bc6bc1c8e4e39b7f
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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