Potassium Hydroxide → 4-Vinylphenol

HRID 2357424Notes

Reaction equation

HRID 2357424 reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10]C(O)=O)=[CH:7][CH:6]=1)(=O)C.[OH-].[K+].C([O-])(=O)C.[NH4+]>>[CH:9]([C:8]1[CH:14]=[CH:15][C:5]([OH:4])=[CH:6][CH:7]=1)=[CH2:10]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 517165Ammonium Acetate

Product 1

HCID 624534-VinylphenolYield 49%

Procedure

A mixture of 4-acetyloxycinnamic acid (0.0083 mol), KOH (10%, 3 ml), ammonium acetate (1 g) and basic alumina (5 g) were taken in a 250 ml Erlenmeyer flask fitted with loose funnel at the top. The flask was placed inside the microwave oven and irradiated for 10 minutes. After completion of reaction the solid mixture washed with ethyl acetate and ethyl acetate layer was washed with dil HCl, water, brine and dried over anhydrous sodium sulphate and purified on silica gel column chromatography using mixture of hexane and ethyl acetate (9:1 to 6:4) provided viscous liquid. 49% yield; 1H NMR (CDCl3) δ 7.31 (2H, d, J=8.48 Hz), 6.81 (2H, d, J=8.48 Hz), 6.67 (1H, dd, J=17.81 and 11.30 Hz), 5.51 (1H, s), 5.2 (1H, d, J=17.81), 5.14 (1H, d, J=11.30 Hz); 13C NMR (CDCl3) δ 155.5, 136.5, 130.9, 128.0, 115.8 and 112.0.

Workup

  1. customfitted with loose funnel at the top
  2. customirradiated for 10 minutes
  3. customAfter completion of reaction the solid mixture
  4. washwashed with ethyl acetate and ethyl acetate layer
  5. washwas washed with dil HCl, water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. custompurified on silica gel column chromatography
  8. additionmixture of hexane and ethyl acetate (9:1 to 6:4)
  9. customprovided viscous liquid

Sources & evidence

ORD record
ord-525e173196ed40bbadce58436293d5ca
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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