3,5-Di-tert-butylcatechol → 3,5-Di-tert-butyl-1,2-benzoquinone

HRID 225205Notes

Reaction equation

HRID 225205 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[C:7]([OH:8])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]>[Ag]=O.CCOCC>[C:1]([C:5]1[C:6](=[O:16])[C:7](=[O:8])[CH:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 660993,5-Di-tert-butylcatechol

Product 1

HCID 769153,5-Di-tert-butyl-1,2-benzoquinone

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5 g. (22.5 mmol.) of 3,5-di-t-butylcatechol in 75 ml. of ether at 0° was added 25 g. of silver oxide. The reaction mixture was stirred at 0° for 30 minutes then at ambient temperature for an additional 30 minutes. The mixture was filtered and the filtrate was evaporated to dryness. Benzene was added to the residue and the resulting precipitate was collected by filtration and air dried to give 3,5-di-t-butyl-1,2-dioxobenzene, m.p. 110°-112°.

Workup

  1. waitat ambient temperature for an additional 30 minutes
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. additionBenzene was added to the residue
  5. filtrationthe resulting precipitate was collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-9e29192a4e5c4bc396343fbfe4430013
Source dataset
uspto-grants-1980_11
Patent number
US04236001

Reaction notes

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