4-Hydroxybenzaldehyde → 4-Vinylphenol

HRID 1611749Notes

Reaction equation

HRID 1611749 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](O)(=O)CC(O)=O>C(O)(=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)=[CH2:10]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 867Malonic Acid

Product 1

HCID 624534-VinylphenolYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (1.0 g, 0.0082 mol), malonic acid (1.69 g, 0.0163 mol), triethylamine(2–4 mL) and acetic acid (10–15 mL) were taken in a 100 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was shaken well and placed inside the microwave oven and irradiated for 2–8 minutes in parts. The cooled mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate, dil HCl., saturated sodium chloride and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain liquid which was purified on silica gel column chromatography using mixture of hexane and ethyl acetate (9:1 to 6:4), provided sweet and pleasant smelling liquid in 40% yield; 1H NMR (CDCl3) δ 7.31 (2H, d, J=8.5 Hz, H-2 and H-6), 6.81 (2H, d, J=8.8 Hz, H-3 and H-5), 6.67 (1H, dd, J=17.8 Hz, 11.3 Hz, (CH═CH2), 5.51 (1H, s, OH), 5.2 (1H, d, J=17.8, cis-CH═CH2), 5.14 (1H, d,J=11.3 Hz, trans-CH═CH2); 13C NMR (CDCl3) δ 155.5 (C-1), 136.5 (CH═CH2), 130.9 (C-4), 128.0 (C-3 and C-5), 115.8 (C-2 and C-6), 112.0 (CH═CH2).

Workup

  1. customfitted with a loose funnel at the top
  2. customirradiated for 2–8 minutes in parts
  3. additionThe cooled mixture was poured into ice cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with sodium bicarbonate, dil HCl
  6. dry with material, saturated sodium chloride and then organic layer dried over sodium sulphate
  7. customThe solvent was evaporated under reduced pressure
  8. customto obtain liquid which
  9. customwas purified on silica gel column chromatography
  10. additionmixture of hexane and ethyl acetate (9:1 to 6:4)
  11. customprovided sweet

Sources & evidence

ORD record
ord-06c7945c53e9435ea529b167b00fe238
Source dataset
uspto-grants-2006_01
Patent number
US06989467B2

Reaction notes

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