Vanillin → 3-(4-Hydroxy-3-methoxyphenyl)-1-phenyl-2-propen-1-one

HRID 716608Notes

Reaction equation

HRID 716608 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=O.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH3:13]>C(O)(=O)C>[OH:11][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 1183VanillinHCID 7410Acetophenone

Product 1

HCID 1460513-(4-Hydroxy-3-methoxyphenyl)-1-phenyl-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-methoxy-4-hydroxybenzaldehyde (20 gm, 0.132 mol) was added to the solution of acetophenone (20 gm, 0.125 mol) dissolved in acetic acid (20 mL) in a round bottom flask with constant stirring. Temperature of reaction was maintained below 15° C. with Occasional shaking for 200 hrs. Reaction mixture was poured in ice cold water and the product was extracted with chloroform. Chloroform extract was distilled under reduced pressure and the residue was chromatographed on SiO2 gel to obtain 1. m.p. 91° C.

Workup

  1. customTemperature of reaction
  2. temperaturewas maintained below 15° C.
  3. customReaction mixture
  4. additionwas poured in ice cold water
  5. extractionthe product was extracted with chloroform
  6. extractionChloroform extract
  7. distillationwas distilled under reduced pressure
  8. customthe residue was chromatographed on SiO2 gel
  9. customto obtain 1

Sources & evidence

ORD record
ord-979f840647cc40cb89eb9b42809b5ac6
Source dataset
uspto-grants-2015_11
Patent number
US09192589B2

Reaction notes

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