Sodium Sulfate → 1-(3,4-Dihydroxy-5-nitrophenyl)ethanone

HRID 1974695Notes

Reaction equation

HRID 1974695 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[O:14]C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C.Br>[OH:14][C:3]1[CH:4]=[C:5]([C:11](=[O:13])[CH3:12])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 2947641-(4-Hydroxy-3-methoxy-5-nitrophenyl)ethanone

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution containing 19.9 g of the product obtained in Example 18 in 200 ml of acetic acid and 200 ml of 48% hydrobromic acid was refluxed for 5 h. 500 ml of a saturated solution of sodium sulfate was added to the reaction mixture and the same was let stand overnight at 5° C. The solution was extracted with ether. The ether phase was washed with 200 ml of water, dried and the solvent evaporated in vacuo. The residue was crystallized from isopropanol. Yield 10.2 g (55%), m.p. 155°-159° C.

Workup

  1. temperaturewas refluxed for 5 h
  2. extractionThe solution was extracted with ether
  3. washThe ether phase was washed with 200 ml of water
  4. customdried
  5. customthe solvent evaporated in vacuo
  6. customThe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-e5fc15c8a57343f68fd71d7641d407aa
Source dataset
uspto-grants-1994_02
Patent number
US05283352

Reaction notes

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