Vanillin → 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

HRID 883439Notes

Reaction equation

HRID 883439 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.O=[CH:14][C:15]1[CH:23]=[CH:22][C:20]([OH:21])=[C:17]([O:18][CH3:19])[CH:16]=1>C(OCCOCCOCC)C>[OH:21][C:20]1[CH:22]=[CH:23][C:15]([CH:14]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([OH:3])=[CH:5][CH:6]=2)=[O:12])=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 1183VanillinHCID 74694'-HydroxyacetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 667388783-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-oneYield 93.8%

Reagents, catalysts & solvents 1

HCID 8179Diethylene glycol diethyl etherSolvent

Procedure

Potassium hydroxide (20 g) in 100 g of diethylene glycol diethyl ether is heated to 120° C. while being stirred, and added to a mixture of 14 g of p-hydroxyacetophenone and 15 g of vanillin within 1 h. Upon completion of the addition stirring is continued for another 20 min., a hydrolysis is carried out and the pH is adjusted to 6-7. After phase separation, the solvent is removed and 25 g of 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propene-1-one is obtained. Yield: 93% of the theory.

Workup

  1. additionUpon completion of the addition
  2. stirringstirring
  3. customAfter phase separation
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-4a69c4a32cfa4679b441d30a28ee7b17
Source dataset
uspto-grants-2012_08
Patent number
US08236859B2

Reaction notes

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