Sodium Dithionite → 2,6-Dimethylhydroquinone

HRID 2108937Notes

Reaction equation

HRID 2108937 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-82dbb4635f4842c3821844e2b5c76cac
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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