Acetone → 1,2,4,5-Benzenetetrol

HRID 1450039Notes

Reaction equation

HRID 1450039 reaction equation
[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([OH:9])[C:6](=[O:8])[CH:7]=1.Cl.CC(C)=O.CC1(C)OC2C=C3OC(C)(C)OC3=CC=2O1>O.[Fe]>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([OH:9])=[CH:4][C:3]=1[OH:10]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 692132,5-Dihydroxy-1,4-benzoquinoneHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)

Product 1

HCID 694641,2,4,5-Benzenetetrol

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

2,5-Dihydroxy-1,4-benzoquinone (10.00 g, 71.43 mmol) was suspended in water (200 ml, distilled) followed by HCl (6 mL, 142.86 mmol, conc.). Iron (4.00 g, 71.43 mmol, powder) was added and the mixture was stirred 30 minutes at room temperature. The solution was filtered and the solution evaporated to dryness. The product was isolated as a grey brown powder containing some iron complexes. Yield 14.80 g. The product is used as such in the reaction with acetone and P2O5 (Example 5) with no negative effects.

Workup

  1. filtrationThe solution was filtered
  2. customthe solution evaporated to dryness
  3. customThe product was isolated as a grey brown powder

Sources & evidence

ORD record
ord-5c79e0b3434342ea8430fc51f22ef561
Source dataset
uspto-grants-1997_02
Patent number
US05599522

Reaction notes

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