Sulfuric Acid → Trimethylhydroquinone

HRID 1656542Notes

Reaction equation

HRID 1656542 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[OH:22].[OH-].[Na+].S(=O)(=O)(O)[OH:26]>O>[CH3:13][C:14]1[C:19]([CH3:20])=[C:18]([OH:26])[C:17]([CH3:21])=[CH:16][C:15]=1[OH:22]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 127692,3,5-TrimethylphenolHCID 14798Sodium HydroxideHCID 24412Potassium Persulfate

Product 1

HCID 12785TrimethylhydroquinoneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution containing 100 mmols of potassium persulfate in one liter of water is added dropwise with stirring, at 20° C., to a solution containing 100 mmols of 2,3,5-trimethylphenol in 100 ml of a 10% solution of sodium hydroxide. After stirring for 20 hours, the reaction mixture is neutralized with concentrated sulfuric acid and the solid formed is filtered. The remaining aqueous solution is acidified by slowly adding 220 ml of concentrated sulfuric acid, and heated for 30 minutes at 80° C. The oil formed is decanted and extracted with ethyl ether. The expected product is obtained after drying the ether phase, evaporating and recrystallizing in ethyl acetate.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring for 20 hours
  3. customthe solid formed
  4. filtrationis filtered
  5. additionby slowly adding 220 ml of concentrated sulfuric acid
  6. temperatureheated for 30 minutes at 80° C
  7. customThe oil formed
  8. customis decanted
  9. extractionextracted with ethyl ether

Sources & evidence

ORD record
ord-12966496ac594b47809326c536502960
Source dataset
uspto-grants-1993_10
Patent number
US05254590

Reaction notes

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