Hydrogen Bromide → HCID 14450998, compound

HRID 274515Notes

Reaction equation

HRID 274515 reaction equation
C[O:2][C:3]1[C:10]([O:11]C)=[CH:9][C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:4]=1[CH:5]=[O:6].Br>C(O)(=O)C>[OH:2][C:3]1[C:10]([OH:11])=[CH:9][C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 2325252,3-dimethoxy-5-nitrobenzaldehyde

Product 1

HCID 14450998HCID 14450998, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.0 g of 2,3-dimethoxy-5-nitrobenzaldehyde are treated with 50 ml of glacial acetic acid and 50 ml of constant-boiling hydrobromic acid and held at the reflux temperature for 7 hours. After treatment with ice the separated precipitate is filtered under suction, washed with water and taken up in ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The crude product obtained is filtered over silica gel with ethyl acetate. After crystallization from ethyl acetate/hexane there is obtained 2,3-dihydroxy-5-nitro-benzaldehyde in the form of brownish crystals of m.p. 226°-228°.

Workup

  1. filtrationAfter treatment with ice the separated precipitate is filtered under suction
  2. washwashed with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe crude product obtained
  6. filtrationis filtered over silica gel with ethyl acetate
  7. customAfter crystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-a41c76297e0f4b4da8f20d00e0294695
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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