Water → 1,4,5,8-Tetra-tert-butylnaphthalene-2,3-dione

HRID 1415341Notes

Reaction equation

HRID 1415341 reaction equation
[C:1]([C:5]1[C:14]2[C:9](=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=[CH:12][C:13]=2[C:15]([CH3:18])([CH3:17])[CH3:16])[C:8]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(=O)(O)[O-:28].[Na+].[OH2:32]>N1C=CC=CC=1.[Os](=O)(=O)(=O)=O>[C:19]([C:10]1[C:11](=[O:28])[C:12](=[O:32])[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[C:14]2[C:9]=1[C:8]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:7][CH:6]=[C:5]2[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 21481801HCID 21481801, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 214818001,4,5,8-Tetra-tert-butylnaphthalene-2,3-dione

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 1049PyridineSolvent2×

Conditions

Temperature
90 °C

Procedure

One stoichiometric equivalent of 1,4,5,8-tetra-t-butyl-naphthalene and one equivalent of osmium tetraoxide (OsO4) in pyridine are stirred for several hours at room temperature (about 20°-25° C). A solution of excess sodium bisulfite (NaHSO3) in pyridine and water is added with stirring. The resulting crude product is extracted with methylene chloride (H2CCL2) and is purified by chromatography on alumina. A resulting 1,4,5,8-tetra-t-butyl-2,3-dihydronaphthalene-2,3-diol is treated with excess copper sulfate (CuSO4) in pyridine and water, is heated to 90° C for several hours, and then is cooled. The mixture is diluted with water and is extracted with an organic solvent (e.g., diethylether, chloroform, or methylene chloride). The solvent is evaporated and the crude product purified by chromatography on alumina to obtain 1,4,5,8-tetra-t-butyl-2,3-dihydronaphthalene-2,3-dione (1,4,5,8-tetra-t-butyl-2,3-naphthoquinone).

Workup

  1. extractionThe resulting crude product is extracted with methylene chloride (H2CCL2)
  2. customis purified by chromatography on alumina
  3. additionA resulting 1,4,5,8-tetra-t-butyl-2,3-dihydronaphthalene-2,3-diol is treated with excess copper sulfate (CuSO4) in pyridine and water
  4. temperatureis cooled
  5. additionThe mixture is diluted with water
  6. extractionis extracted with an organic solvent (e.g., diethylether, chloroform, or methylene chloride)
  7. customThe solvent is evaporated
  8. customthe crude product purified by chromatography on alumina

Sources & evidence

ORD record
ord-b1f99e77bdf94a2fb7f4c1d8d8139e60
Source dataset
uspto-grants-1977_01
Patent number
US04004571

Reaction notes

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