Dimethyl Sulfoxide → 1,3,6,8-tetrachlorodibenzo-p-dioxin

HRID 439747Notes

Reaction equation

HRID 439747 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:4]=1[OH:11].[CH3:12]S(C)=O>>[C:4]1([O:11][CH3:12])[CH:5]=[CH:6][CH:7]=[CH:8][CH:3]=1.[CH3:4][OH:11].[Cl:10][C:5]1[C:4]2[O:11][C:3]3[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:4]=3[O:11][C:3]=2[CH:8]=[C:7]([Cl:9])[CH:6]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 69142,4,6-TrichlorophenolHCID 5360545Sodium

Product 2

HCID 364741,3,6,8-tetrachlorodibenzo-p-dioxinYield 1%HCID 86749479HCID 86749479, compound

Procedure

This is a prophetic example. 2.5 gms. of the sodium salt of 2,4,6-trichlorophenol and 5 to 7 mls. of dimethylsulfoxide are stirred at 200-200° C. for 16-24 hours. The reaction mixture is adsorbed on 10 gms. of silica gel, the solvent is allowed to evaporate and the absorbed reaction mixture is placed on top of a silica gel column (60 gms. silica gel, 4×2 mm). The column is eluted with 500 mls. of petroleum spirit. The solvent is removed in vacuo and the residue is recrystallized from 4 mls. of anisole/methanol (1:9) to give a 1-10% yield of 1,3,6,8-tetrachlorodibenzo-p-dioxin. The minor product 1,3,7,9-tetrachlorodibenzo-p-dioxin (2,4,6,8-tetrachlorodibenzo-p-dioxin) can be recovered from the mother liquors and further purified by high pressure liquid chromatography or by recrystallization from anisole/methanol.

Workup

  1. customto evaporate
  2. customthe absorbed reaction mixture
  3. washThe column is eluted with 500 mls
  4. customThe solvent is removed in vacuo
  5. customthe residue is recrystallized from 4 mls

Sources & evidence

ORD record
ord-1f5d9fc94c114bdea32675dbbbdbb64d
Source dataset
uspto-grants-1996_05
Patent number
US05516790

Reaction notes

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