Sulfuric Acid → HCID 23442865, compound

HRID 2186265Notes

Reaction equation

HRID 2186265 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](O)=[O:20].S(=O)(=O)(O)O>C(#N)C>[C:1]([C:5]1[CH:11]=[C:10]([O:12][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17])[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23742,5-Di-tert-butylhydroquinoneHCID 6417Pivalic acid

Product 1

HCID 23442865HCID 23442865, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under argon atmosphere, a solution of 11.12 g of 2,5-di-t-butylhydroquinone and 10.1 ml of anhydrous trimethylacetic acid in 200 ml of acetonitrile was stirred with a catalytic amount of sulfuric acid at room temperature for a whole day and night. After the reaction mixture was evaporated under reduced pressure, the concentrate was dissolved in diisopropyl ether. This solution was washed with a saturated aqueous sodium bicarbonate solution, then saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 5% ethyl acetate) to give 11.9 g of 2,5-di-t-butyl-4-trimethylacetoxyphenol as a white solid (yield 78%).

Workup

  1. customAfter the reaction mixture was evaporated under reduced pressure
  2. dissolutionthe concentrate was dissolved in diisopropyl ether
  3. washThis solution was washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 5% ethyl acetate)

Sources & evidence

ORD record
ord-e0738222c91f4aa6a10c240d4ec708b9
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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