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

HRID 1464487Notes

Reaction equation

HRID 1464487 reaction equation
C(OC1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.[OH-].[K+].C(O[C:20]([O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=O)(C)(C)C>[OH-].[K+].CO>[C:26]([O:25][C:23]([O:22][C:20]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][CH:6]=1)=[O:24])([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 3

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

Product 1

HCID 934851,1-Dimethylethyl 4-ethenylphenyl carbonateYield 85%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
12 °C

Procedure

A solution comprising 2.4 grams of potassium hydroxide, 201 grams 4-acetoxystyrene and 500 grams of methanol was heated at reflux for 2.2 hours. The reaction was cooled to 12° C. and 64 grams potassium hydroxide pellets were added over a period of 10 minutes. After warming to 25° C., 314 grams di-tertiary-butyl-dicarbonate was introduced over a period of one hour. After an additional 2.3 hours of reaction time, the reaction slurry was washed with water and extracted with ethyl acetate. The ethyl acetate was stripped from the extraction mixture using a rotary evaporator, and the residual oil was charged with 0.26 grams phenothiazine inhibitor. Distillation at 0.1 Mm Hg yielded 227.2 grams (85% yield) 4-tertiarybutoxycarbonyloxystyrene.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.2 hours
  3. temperatureAfter warming to 25° C.
  4. customAfter an additional 2.3 hours of reaction time
  5. washthe reaction slurry was washed with water
  6. extractionextracted with ethyl acetate
  7. customa rotary evaporator
  8. additionthe residual oil was charged with 0.26 grams phenothiazine
  9. distillationDistillation at 0.1 Mm Hg

Sources & evidence

ORD record
ord-61b35585306c40be9cc604545fac4647
Source dataset
uspto-grants-1994_04
Patent number
US05304690

Reaction notes

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