Acetic Acid → p-Tert-butoxyphenol

HRID 1609754Notes

Reaction equation

HRID 1609754 reaction equation
C([Li])(CC)C.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=1.C([O:21]B(OC(C)C)OC(C)C)(C)C.C(O)(=O)C.OO>C1COCC1>[C:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([OH:21])=[CH:8][CH:9]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 21531Triisopropyl borateHCID 27639591-Bromo-4-(tert-butoxy)benzeneHCID 178418400CID 53628100

Product 1

HCID 2773621p-Tert-butoxyphenolYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Sec-butyllithium (53.2 mmoles, 41 ml of 1.3M in hexane) was added dropwise at -78° C. to 4-bromo-t-butoxybenzene (53.2 mmoles, 12.2 g) in 200 ml THF, stirred at -78° C. for 1 hour, and added slowly to a solution of triisopropylborate (58.5 mmoles, 11.0 g) in 50 ml THF while maintaining the temperature below -60° C. The mixture was allowed to warm gradually to -20° C. Chilled acetic acid (80 mmoles,9.6 ml) was added. Hydrogen peroxide (58.5 mmoles, 5.9 ml of 30% diluted with 5 ml water) was added dropwise over 15 minutes while maintaining the temperature below 0° C. After stirring 10 minutes, the solution was washed with ammonium sulfate solution, dried, and concentrated. The residue was triturated with hexane and filtered to yield 4.2 g of 4-t-butoxyphenol. (MS).

Workup

  1. temperaturewhile maintaining the temperature below -60° C
  2. temperatureto warm gradually to -20° C
  3. temperaturewhile maintaining the temperature below 0° C
  4. stirringAfter stirring 10 minutes
  5. washthe solution was washed with ammonium sulfate solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was triturated with hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-b1a29195acd14ee3ad911145b12ee7f6
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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