Sodium Iodide → 3-(3-Methoxy-4-phenylmethoxyphenyl)prop-2-enal

HRID 1059032Notes

Reaction equation

HRID 1059032 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=[O:9])=[CH:4][C:3]=1[O:12][CH3:13].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(C)=O>[CH2:14]([O:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=[O:9])=[CH:4][C:3]=1[O:12][CH3:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 99842-Propenal, 3-(4-hydroxy-3-methoxyphenyl)-HCID 11430Potassium Carbonate

Product 1

HCID 537901463-(3-Methoxy-4-phenylmethoxyphenyl)prop-2-enalYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxy-3-methoxycinnamaldehyde (0.6 g) was added to the mixture of benzyl chloride (1 mL), K2CO3 (1 g), and NaI (1 g) in acetone (20 mL). The resulting mixture was stirred at room temperature for 24 hrs. The solid were removed by filtration and washed with acetone. After evaporation of solvent, the crude product was purified by gradient chromatography to give a yellowish solid. Yield 85%.

Workup

  1. customThe solid were removed by filtration
  2. washwashed with acetone
  3. customAfter evaporation of solvent
  4. customthe crude product was purified by gradient chromatography
  5. customto give a yellowish solid

Sources & evidence

ORD record
ord-fbb54ea6072e472ebc9d8fcc69187f33
Source dataset
uspto-grants-2003_02
Patent number
US06518315B1

Reaction notes

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