Diethyl Ether → 1,2,4-Benzenetriol

HRID 1902888Notes

Reaction equation

HRID 1902888 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]C(=O)C)=[CH:7][C:6]=1[O:15]C(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>CO.S(=O)(=O)(O)O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:15]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 691691,2,4-Triacetoxybenzene

Product 1

HCID 107871,2,4-Benzenetriol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

Eighty grams of the crude 1,2,4-triacetoxybenzene were dissolved in 200 ml of methanol containing 6 g of concentrated sulfuric acid. The reaction mixture was boiled under reflux for one hour. Then the solution was cooled to room temperature and neutralized with an equivalent amount of fine powdered sodium carbonate. Thereafter 800 ml of ethylether was added whereupon sodium sulfate precipitated out, which was removed by filtration. Reaction by-products and contaminants being responsible for a dark red coloration may be removed employing solid silica gel. After evaporation of the supernatant under reduced pressure, a dark red oil is obtained which crystallized upon standing at 40° C. in the form of a slight reddish solid mass which is pure enough for the next step. This product is 1,2,4-trihydroxybenzene.

Workup

  1. temperatureunder reflux for one hour
  2. customprecipitated out
  3. customwhich was removed by filtration
  4. customReaction by-products and contaminants
  5. custommay be removed
  6. customAfter evaporation of the supernatant under reduced pressure
  7. customa dark red oil is obtained which
  8. customcrystallized
  9. customupon standing at 40° C. in the form of a slight reddish solid mass which

Sources & evidence

ORD record
ord-d869b5efa818473c99807dd478be86a5
Source dataset
uspto-grants-1982_12
Patent number
US04366248

Reaction notes

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