Vanillin → 3-Chloro-4-hydroxy-5-methoxybenzaldehyde

HRID 705698Notes

Reaction equation

HRID 705698 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(O)(=O)C>[Cl:12][C:10]1[CH:11]=[C:3]([CH:4]=[C:5]([O:6][CH3:7])[C:8]=1[OH:9])[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 1183VanillinHCID 24526Chlorine

Product 1

HCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehydeYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 50.0 g (330 mmol) of vanillin in 250 mL of glacial acetic acid was added chlorine gas through a glass tubing over 60 minutes (with a slow gas flow) at 25° C. White solid product was collected by filtration, washed with 300 mL of hexane, and dried in vacuum to give the title compound (36.0 g; 58%).

Workup

  1. filtrationWhite solid product was collected by filtration
  2. washwashed with 300 mL of hexane
  3. customdried in vacuum

Sources & evidence

ORD record
ord-c839d6d2941046ada8b17fd497fd69d5
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

Loading…