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

HRID 1059031Notes

Reaction equation

HRID 1059031 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

4

Reactant 3

HCID 180AcetoneHCID 1183VanillinHCID 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%).

Workup

  1. extractionAfter acidification the product was extracted with EtOAc twice
  2. washwashed with water
  3. customEvaporation of solvent
  4. waitleft a dark brown liquid which
  5. customon crystallisation from EtOAc-petroleum

Sources & evidence

ORD record
ord-a175496794fa49c284e1446c0f652d36
Source dataset
uspto-grants-2003_02
Patent number
US06518315B1

Reaction notes

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