3,4-Dimethoxy-5-nitrobenzophenone → 3,4-Dihydroxy-5-nitrobenzophenone

HRID 274442Notes

Reaction equation

HRID 274442 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[O:17]C)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]>C(O)(=O)C.Br>[OH:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[OH:17])[C:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7]

Participants

4

Reactant 1

HCID 214590553,4-Dimethoxy-5-nitrobenzophenone

Product 1

HCID 57479693,4-Dihydroxy-5-nitrobenzophenone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

0.5 g of 3,4-dimethoxy-5-nitrobenzophenone is stirred at 110° for 30 hours in a mixture of 4 ml of acetic acid and 4 ml of 48 percent aqueous hydrobromic acid. The reaction mixture is subsequently evaporated to dryness. The residue is taken up in methylene chloride. It is washed with water, dried over sodium sulfate and evaporated. After recrystallization from methylene chloride/hexane there is obtained 3,4-dihydroxy-5-nitrobenzophenone of m.p. 132°.

Workup

  1. customThe reaction mixture is subsequently evaporated to dryness
  2. washIt is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customAfter recrystallization from methylene chloride/hexane there

Sources & evidence

ORD record
ord-37df08a5c8e54831b971f5968657e721
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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