Hydrogen Peroxide → 1,2,3-Benzenetriol, 5-methyl-

HRID 1703405

Reaction equation

HRID 1703405 reaction equation
[OH:1][C:2]1[C:9](C=O)=[CH:8][C:7]([CH3:12])=[CH:6][C:3]=1C=O.[OH-:13].[Na+].[OH:15]O>O>[CH3:12][C:7]1[CH:6]=[C:3]([OH:15])[C:2]([OH:1])=[C:9]([CH:8]=1)[OH:13]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 817442,6-Diformyl-4-methylphenol

Product 1

HCID 5877901,2,3-Benzenetriol, 5-methyl-Yield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Under a nitrogen atmosphere throughout: 5.3 Parts of 2-hydroxy-5-methylisophthalaldehyde prepared in Example 15 or 16 were slurried with a solution of 2.6 parts of sodium hydroxide in 32 parts of water, and a solution of 9.8 parts of 27.2% by weight hydrogen peroxide in 35 parts of water was added over four minutes. The temperature rose to 85° C. initially and was then maintained at 40°-50° C. with external cooling. After a further 18 minutes the pH was 7.8. The solution was filtered to remove 1.05 parts of unchanged starting material, and the filtrate was continuously extracted with ether to give 2.5 parts of 5-methylpyrogallol, m.pt. 114°-121° C., equivalent to 69% yield.

Workup

  1. customrose to 85° C.
  2. temperaturewas then maintained at 40°-50° C. with external cooling
  3. filtrationThe solution was filtered
  4. customto remove 1.05 parts
  5. extractionthe filtrate was continuously extracted with ether

Sources & evidence

ORD record
ord-25d26f2d951f49f2ad2f279cbe6813ef
Source dataset
uspto-grants-1982_09
Patent number
US04351968

Linked notes

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