Sodium Dithionite → 2,3-Dimethoxybenzene-1,4-diol

HRID 993260Notes

Reaction equation

HRID 993260 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][O:10][C:11]1[C:12](=[O:20])[CH:13]=[CH:14][C:15](=[O:19])[C:16]=1[O:17][CH3:18]>CO.O>[CH3:18][O:17][C:16]1[C:11]([O:10][CH3:9])=[C:12]([OH:20])[CH:13]=[CH:14][C:15]=1[OH:19]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 765652,3-Dimethoxy-p-benzoquinone

Product 1

HCID 137437552,3-Dimethoxybenzene-1,4-diolYield 39.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydrosulphite (Na2S2O4, 26 g) was added portionwise to a stirred solution of 2,3-dimethoxy-1,4-benzoquinone (J. Med. Chem., 1971, 14, 45; 5 g) in a mixture of methanol (50 ml) and water (100 ml). The resultant mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated to give 2,3-dimethoxyhydroquinone (2 g); NMR Spectrum: (CD3SOCD3) 3.71 (s, 6H), 6.37 (s, 2H), 8.47 (s, 2H).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-521b2e7caf214767985f0d9c72762ef7
Source dataset
uspto-grants-2002_10
Patent number
US06472435B1

Reaction notes

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