Sodium Dithionite → 2,3-Dimethoxy-5-methyl-1,4-benzenediol

HRID 2268436

Reaction equation

HRID 2268436 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][O:10][C:11]1[C:12](=[O:21])[CH:13]=[C:14]([CH3:20])[C:15](=[O:19])[C:16]=1[O:17][CH3:18]>O.C(OCC)C>[CH3:20][C:14]1[C:15]([OH:19])=[C:16]([O:17][CH3:18])[C:11]([O:10][CH3:9])=[C:12]([OH:21])[CH:13]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 690682,3-Dimethoxy-5-methyl-1,4-benzoquinone

Product 1

HCID 111830272,3-Dimethoxy-5-methyl-1,4-benzenediolYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of sodium dithionite (95.4 g, 0.548 mols) in water (330 ml) was added to a solution of 2,3-dimethoxy-5-methyl-1,4-benzoquinone (50 g, 0.274 mols) in diethyl ether (330 ml), and shaken for 15 minutes. The ether layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated in vacuo. The resulting crystals were washed with hexane to obtain 2,3-dimethoxy-5-methyl-1,4-hydroquinone (46.1 g).

Workup

  1. washThe ether layer was washed with a saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. washThe resulting crystals were washed with hexane

Sources & evidence

ORD record
ord-d8f3fca6a57144dd85f4d45896d3b8a5
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Linked notes

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