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

HRID 1657217Notes

Reaction equation

HRID 1657217 reaction equation
[OH-].[K+].[C:3]([O:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(OC(C)(C)C)=O.C(OC1[CH:29]=[CH:28][C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=1)(=O)C>CO.C(OCC)(=O)C>[C:14]([O:13][C:11]([O:10][C:3]1[CH:27]=[CH:26][C:25]([CH:28]=[CH2:29])=[CH:24][CH:23]=1)=[O:12])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 3

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

Product 1

HCID 934851,1-Dimethylethyl 4-ethenylphenyl carbonateYield 103.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 85 grams (1.3 moles) of potassium hydroxide in 161 grams of methanol was added in periodic additions along with 229 grams (1.0 moles) of di-t-butyl dicarbonate to a stirred solution of 101 grams (0.65 moles) of 4-acetoxystyrene in 505 grams of ethyl acetate over a period of about 40 minutes. The reagents were added concurrently in approximately equal aliquots while the reaction mixture wa kept at 25° C. with an ice bath. After an additional 2 hours of reaction at 25° C., the reaction slurry was washed well with water to remove solids. The volatile components of the organic layer were stripped under vacuum to give 148 grams (83% crude yield) of 4-tertiary-butoxycarbonyloxystyrene. Vacuum distillation afforded 87 grams (65% yield) of pure product, b.p. 111° C./0.25 mm.

Workup

  1. additionThe reagents were added concurrently in approximately equal aliquots while the reaction mixture
  2. customwa kept at 25° C. with an ice bath
  3. customAfter an additional 2 hours of reaction at 25° C.
  4. washthe reaction slurry was washed well with water
  5. customto remove solids

Sources & evidence

ORD record
ord-8ca31c13e23a45d6ba14d1e35d8315b7
Source dataset
uspto-grants-1993_10
Patent number
US05256809

Reaction notes

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