Bromide ion → 1,1-Dimethylethyl 4-ethenylphenyl carbonate

HRID 2412347Notes

Reaction equation

HRID 2412347 reaction equation
[Br-].[CH3:2]C(C)([O-])C.[K+].[C:8]([O:12][C:13]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].O>C1COCC1>[C:8]([O:12][C:13]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH2:2])=[CH:18][CH:17]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 962WaterHCID 688201tert-Butyl 4-formylphenyl carbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 934851,1-Dimethylethyl 4-ethenylphenyl carbonateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 34.1 g of methylriphenylphosphonium bromide in 400 mL of dry THF was treated with 10.7 g of potassium t-butoxide under a nitrogen atmosphere. After stirring for 10 min at room temperature, the yellow solution was treated with a solution of 21.2 g of p-t-butoxycarbonyloxybenzaldehyde in 100 mL of dry THF. After stirring for one hour, the mixture was poured into cold water and extracted with ethyl acetate. The organic phase was washed, dried over magnesium sulfate and concentrated. The crude product was purified by preparative HPLC to yield 16.6 g (79%) of pure p-t-butoxycarbonyloxystyrene. Alternately, IIIc was purified by distillation under reduced pressure.

Workup

  1. stirringAfter stirring for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f5a916d278d041a2a76740e6bb1d195d
Source dataset
uspto-grants-1985_01
Patent number
US04491628

Reaction notes

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