Carbon Dioxide → 4-Vinylphenol

HRID 2073704Notes

Reaction equation

HRID 2073704 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7]C(O)=O)=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1.C1(C=CC(O)=CC=1)O.C(=O)=O>[Cu]>[CH:6]([C:5]1[CH:11]=[CH:12][C:2]([OH:1])=[CH:3][CH:4]=1)=[CH2:7]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3224-Coumaric acidHCID 785HydroquinoneHCID 7047Quinoline

Product 1

HCID 624534-VinylphenolYield 11.76%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Para-vinylphenol was prepared as follows. 15.6 g of p-hydroxycinnamic acid were mixed to a slurry with 15 ml quinoline, 0.6 g copper turnings and 1.1 g hydroquinone. The mixture was heated by an oil bath at 200° C. for 15 minutes after which time the evolution of CO2 had almost ceased. The reaction mixture was then cooled and distilled under rotary pump vacuum, the fraction collected between 60° and 80° C. being p-vinylphenol and quinoline. (Bpt. Quinoline=114° C./15 mm Hg; p-vinylphenol=115° C./16 mm Hg). The distilled fraction was taken up into warm diethyl ether, the solution neutralised by successive washing of N HCl and distilled water and then dried by MgSO4. After removal of the solvent, the residue was redissolved by warm petroleum ether (40°-60° C.). On cooling 1.36 g of colourless, platey crystals were obtained. Yield=11.76%. These were recrystallised from the same solvent prior to copolymerisation.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. distillationdistilled under rotary pump vacuum
  3. customthe fraction collected between 60° and 80° C.
  4. custom(Bpt. Quinoline=114° C./15 mm Hg; p-vinylphenol=115° C./16 mm Hg)
  5. temperatureinto warm diethyl ether
  6. washby successive washing of N HCl
  7. distillationdistilled water
  8. dry with materialdried by MgSO4
  9. customAfter removal of the solvent
  10. dissolutionthe residue was redissolved
  11. temperatureby warm petroleum ether (40°-60° C.)
  12. temperatureOn cooling 1.36 g of colourless, platey crystals
  13. customwere obtained
  14. customThese were recrystallised from the same solvent
  15. customto copolymerisation

Sources & evidence

ORD record
ord-db02ef3607d44327b461af74094675c5
Source dataset
uspto-grants-1990_04
Patent number
US04920092

Reaction notes

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