Potassium Hydroxide → 1,1-Dimethylethyl 4-ethenylphenyl carbonate

HRID 2255790Notes

Reaction equation

HRID 2255790 reaction equation
[OH-].[K+].C(OC1[CH:14]=[CH:13][C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=1)(=O)C.C(O[C:20]([O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=O)(C)(C)C>C(O)C>[C:26]([O:25][C:23]([O:22][C:20]1[CH:12]=[CH:11][C:10]([CH:13]=[CH2:14])=[CH:9][CH:8]=1)=[O:24])([CH3:27])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 758214-Ethenylphenyl acetateHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 934851,1-Dimethylethyl 4-ethenylphenyl carbonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
28 °C

Procedure

A solution comprising 0.49 g potassium hydroxide, 40 g of 4-acetoxystyrene, and 100 g of absolute ethanol was refluxed for 4 hours. The reaction solution was cooled to 28° C. and 13 g potassium hydroxide pellets were added over a period of 10 minutes. After an additional 30 minutes of reaction, 64 g di-tertiary-butyl-dicarbonate was charged portionwise over 20 minutes and the reaction was stirred for an additional hour at 28° C.. After aqueous washing, the reaction product was extracted with ethyl acetate. The ethyl acetate was stripped from the extraction mixture on a rotary evaporator and the residual oil was charged with 0.07 g phenothiazine. Distillation at 0.1 mm Hg gave 34.2 (64%) 4-tertiary-butoxycarbonyloxystyrene (IV).

Workup

  1. temperaturewas refluxed for 4 hours
  2. additionwas charged portionwise over 20 minutes
  3. extractionAfter aqueous washing, the reaction product was extracted with ethyl acetate
  4. customThe ethyl acetate was stripped from the extraction mixture on a rotary evaporator
  5. additionthe residual oil was charged with 0.07 g phenothiazine
  6. distillationDistillation at 0.1 mm Hg

Sources & evidence

ORD record
ord-8fca236e1667465a9d0c5dccc5c11808
Source dataset
uspto-grants-1993_08
Patent number
US05241098

Reaction notes

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