Vanillin → HCID 178493653, compound

HRID 1067301Notes

Reaction equation

HRID 1067301 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[Cl:12]Cl>C(Cl)(Cl)Cl>[Cl:12][C:5]1([O:6][CH3:7])[C:8]([OH:9])=[CH:10][CH:11]=[C:3]([CH:2]=[O:1])[CH2:4]1

Participants

4

Reactant 2

HCID 1183VanillinHCID 24526Chlorine

Product 1

HCID 178493653HCID 178493653, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Vanillin (100 g) is dissolved in chloroform (800 ml), and thereto is blown with stirring chlorine gas at room temperature for about one hour to give the white solid. The compressed air is blown into the mixture to remove the chlorine being dissolved therein, and the precipitated solid is collected by filtration, washed, and dried. The mother liquor is concentrated, and triturated with diethyl ether, and the precipitates are collected by filtration, washed, and dried. The former precipitated solid and the powder thus obtained are combined to give 3-chlorovanillin (115.25 g).

Workup

  1. customto give the white solid
  2. customto remove the chlorine being
  3. dissolutiondissolved
  4. filtrationthe precipitated solid is collected by filtration
  5. washwashed
  6. customdried
  7. concentrationThe mother liquor is concentrated
  8. customtriturated with diethyl ether
  9. filtrationthe precipitates are collected by filtration
  10. washwashed
  11. customdried
  12. customThe former precipitated solid
  13. customthe powder thus obtained

Sources & evidence

ORD record
ord-1f39197c0d674d85b40e00b9f7d6e81f
Source dataset
uspto-grants-2001_06
Patent number
US06248743B1

Reaction notes

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