Acetone → (3E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one

Reaction equation

O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[OH-].[Na+].[CH3:14][C:15]([CH3:17])=[O:16]>>[CH3:14][C:15](/[CH:17]=[CH:2]/[C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1)=[O:16]

Participants

Reactant 3

HCID 180Acetone

HCID 1183Vanillin

HCID 14798Sodium Hydroxide

Product 1

HCID 5354238(3E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneYield 85%

Procedure

To a solution of vanillin (5 g) in acetone (20 mL) was added 10% sodium hydroxide solution (20 mL). The reaction mixture was stirred at room temperature for 4 days (Normura, 1917). After acidification the product was extracted with EtOAc twice and washed with water. Evaporation of solvent left a dark brown liquid which on crystallisation from EtOAc-petroleum afforded the title compound (85%).