Hydrogen Bromide → 1-(3,4-Dihydroxy-5-nitrophenyl)ethanone

HRID 274444Notes

Reaction equation

HRID 274444 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14](=[O:16])[CH3:15])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.Br>>[OH:2][C:3]1[CH:4]=[C:5]([C:14](=[O:16])[CH3:15])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[OH:9]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 41514731-(3,4-Dimethoxy-5-nitrophenyl)ethanone

Product 1

HCID 144509971-(3,4-Dihydroxy-5-nitrophenyl)ethanone

Procedure

2 g of 3',4'-dimethoxy-5'-nitroacetophenone are treated with 30 ml of constant-boiling hydrobromic acid and stirred at 140° for 2.5 hours. After cooling the mixture is poured into 200 ml of ice-water and extracted three times with 100 ml of ethyl acetate each time. The organic phase is washed twice with 25 ml of sodium chloride solution each time, dried over sodium sulfate and evaporated. The product obtained is filtered with ethyl acetate over a 20-fold amount of silica gel. By recrystallization of the material obtained from water there is obtained 3',4'-dihydroxy-5'-nitroacetophenone in the form of yellow crystals of m.p. 159°-160°.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted three times with 100 ml of ethyl acetate each time
  3. washThe organic phase is washed twice with 25 ml of sodium chloride solution each time
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe product obtained
  7. filtrationis filtered with ethyl acetate over a 20-fold amount of silica gel
  8. customBy recrystallization of the material
  9. customobtained from water

Sources & evidence

ORD record
ord-9197a21d386d4a46861a3fce2cc26afd
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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