Water → HCID 22733940, compound

HRID 1057926Notes

Reaction equation

HRID 1057926 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17].O>CN(C=O)C>[CH2:17]([O:10][C:9]1[C:2]([Br:1])=[C:3]([CH:6]=[CH:7][C:8]=1[O:11][CH3:12])[CH:4]=[O:5])[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 2240112-Bromoisovanillin

Product 1

HCID 22733940HCID 22733940, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-3-hydroxy-4-methoxybenzaldehyde (1.68 g) was dissolved in DMF (17 ml), and sodium hydride (0.209 g) was added thereto under ice-cooling, followed by stirring for 30 minutes. Allyl bromide (0.944 ml) was added to the mixture, followed by stirring at 60° C. for one hour. After being allowed to stand for cooling, water was added to the mixture and the precipitated solid was collected by filtration. The obtained crude crystals were recrystallized from isopropanol to give Compound IIe-a (1.30 g, 66%).

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring at 60° C. for one hour
  3. temperaturefor cooling
  4. filtrationthe precipitated solid was collected by filtration
  5. customThe obtained crude crystals
  6. customwere recrystallized from isopropanol
  7. customto give Compound IIe-a (1.30 g, 66%)

Sources & evidence

ORD record
ord-17f6967fe44349d289b0267b7404f026
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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