Tetramethylammonium hydroxide → 1,1-Dimethylethyl 4-ethenylphenyl carbonate

HRID 1873103Notes

Reaction equation

HRID 1873103 reaction equation
C(OC1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.[OH-].C[N+](C)(C)C.[C:19]([O:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(OC(C)(C)C)=O.OC1C=CC(C=C)=CC=1>>[C:30]([O:29][C:27]([O:26][C:19]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][CH:6]=1)=[O:28])([CH3:31])([CH3:32])[CH3:33]

Participants

5

Reactant 4

HCID 60966Tetramethylammonium hydroxideHCID 624534-VinylphenolHCID 758214-Ethenylphenyl acetateHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 934851,1-Dimethylethyl 4-ethenylphenyl carbonateYield 87%

Procedure

10.00 gs (6.17×10-2 moles) of 4-acetoxystyrene was added to a 25 wt % solution of tetramethylammonium hydroxide (52 mL, 15% mole excess). After stirring for 15 minutes, a clear yellowish solution was obtained. To this solution was added with stirring to mix the phases 13.46 gs (6.17×10-2 moles) of di-tert-butyl dicarbonate. Slow formation of product was observed during 1 to 2 hours and the reaction essentially reached completion after 5 hours. A slight amount of residual 4-hydroxystyrene was detected by thin layer chromotography. The reaction mixture was extracted with two (15 mL) portion of ethyl ether. The ethyl ether extract was washed with 10 mL of 25% tetramethylammonium hydroxide(TMAH) and distilled water to remove base. The organic layer was dried over MgSO4 filtered and the solvent removed under vacuum yielding 11.87 gs (87% yield) of pure 4-tert-butyloxycarbonyloxystyrene. Analysis of the product indicated: IR(cm-1): 2950, 1755, 1275, 1150; 1H NMR(CDCl3, ppm): 1.54(s, 9H), 5.20(d(11 Hz), 1H), 5.67(d(18 Hz), 1H), 6.67(d of d(11, 18 Hz), 1H), 7.11(d(8 Hz), 2H); 7.38(d(8Hz), 2H).

Workup

  1. customa clear yellowish solution was obtained
  2. additionTo this solution was added
  3. stirringwith stirring
  4. waitwas observed during 1 to 2 hours
  5. customthe reaction essentially reached completion after 5 hours
  6. extractionThe reaction mixture was extracted with two (15 mL) portion of ethyl ether
  7. extractionThe ethyl ether extract
  8. washwas washed with 10 mL of 25% tetramethylammonium hydroxide(TMAH)
  9. distillationdistilled water
  10. customto remove base
  11. dry with materialThe organic layer was dried over MgSO4
  12. filtrationfiltered
  13. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-f28b1ef9723e44aba36825aec5c3a30d
Source dataset
uspto-grants-2000_08
Patent number
US06111133

Reaction notes

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