Sulfuric Acid → 4-Acetoxy-3,5-di-tert-butylanisole

HRID 1376970Notes

Reaction equation

HRID 1376970 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([O:12][CH3:13])=[CH:4][C:3]=1[C:14]([CH3:17])([CH3:16])[CH3:15].S(=O)(=O)(O)O.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([O:1][C:2]1[C:3]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[CH:6][C:7]=1[C:8]([CH3:10])([CH3:11])[CH3:9])(=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 102692,6-Di-tert-butyl-4-methoxyphenol

Product 1

HCID 118219544-Acetoxy-3,5-di-tert-butylanisoleYield 88%

Conditions

Temperature
70 °C

Procedure

4-Hydroxy-3,5-di-tert-butylanisole (23.6 g) was dissolved in acetic anhydride (150 ml). Following the addition of conc. sulfuric acid (0.5 ml), the mixture was stirred at 70° C. for 2 h. The reaction mixture was concentrated under reduced pressure and a saturated aqueous solution of sodium hydrogen carbonate was added to the concentrate, followed by extraction with ethyl acetate. The extracted layer was dried over anhydrous magnesium acetate and concentrated. The precipitating solid was recrystallized from methanol-water (2:1) to afford 4-acetoxy-3,5-di-tert-butylanisole [24.5 g (yield, 88%)] as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogen carbonate was added to the concentrate
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extracted layer was dried over anhydrous magnesium acetate
  5. concentrationconcentrated
  6. customThe precipitating solid was recrystallized from methanol-water (2:1)

Sources & evidence

ORD record
ord-a773380efd9c488a9a57a74e170f0968
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

Loading…