Veratraldehyde → HCID 11042902, compound

HRID 567880Notes

Reaction equation

HRID 567880 reaction equation
BrBr.C[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13]C)[CH:8]=[O:9].S([O-])([O-])(=O)=S.[Na+].[Na+].[C:22](=[O:25])(O)[O-].[Na+]>C(O)(=O)C>[OH:13][C:12]1[C:5]([OH:4])=[CH:6][C:7]2[C:8](=[O:9])[CH2:10][C:11]3[CH:12]=[CH:5][CH:6]=[CH:7][C:22]=3[O:25][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 8419VeratraldehydeHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 516892Sodium Bicarbonate

Product 1

HCID 11042902HCID 11042902, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.96 g) in acetic acid (10 ml) was dropped into a solution of 3,4-dimethoxybenzaldehyde (1.0 g) in acetic acid (4 ml) and the mixture was stirred for three hours. Sodium thiosulfate was added to the reaction mixture, then sodium bicarbonate was added thereto and the mixture was filtered. The crude crystals collected by the filtration were recrystallized from chloroform-ether to give the title compound (0.83 g, 56%). The peaks of this compound in 1H-NMR (400 MHz, CDCl3) were as follows.

Workup

  1. filtrationthe mixture was filtered
  2. filtrationThe crude crystals collected by the filtration
  3. customwere recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-00012af593d74fa8a7c5938e51fe119a
Source dataset
uspto-grants-2001_01
Patent number
US06180659B2

Reaction notes

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