Sodium Dithionite → 2,6-Dimethylhydroquinone

HRID 1631060Notes

Reaction equation

HRID 1631060 reaction equation
[CH3:1][C:2]1[C:3](=[O:10])[C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 682412,6-Dimethyl-1,4-benzoquinone

Product 1

HCID 695602,6-DimethylhydroquinoneYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,6-dimethyl-[1,4]benzoquinone (5 g) and sodium hydrosulfite (10 g) in EtOAc (50 mL) and water (20 mL) was stirred for 30 min. After separation with EtOAc, the organic phase was dried and evaporated to dryness to give a off-white solid 5 g of 2,6-dimethyl-benzene-1,4-diol. The solid was dissolved in dry ether, cooled in an ice-water bath, followed by dropwise addition of sulfuryl chloride (5 g). After stirring the solution at RT for 3 h, workup and purification on silica gel column chromatography (30% EtOAc in hexane) gave 2.2 g 2-chloro-3,5-dimethyl-benzene-1,4-diol.

Workup

  1. customAfter separation with EtOAc
  2. customthe organic phase was dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f9f984bac65a40f599827533cae5a159
Source dataset
uspto-grants-2014_07
Patent number
US08791155B2

Reaction notes

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