Chloroform → 3,5-Dichloro-2,6-dimethoxybenzoic Acid

HRID 224418

Reaction equation

HRID 224418 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1C=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:9]=1[C:10]([OH:12])=[O:11].[CH:19]([Cl:22])(Cl)Cl>>[Cl:4][C:14]1[C:13]([O:17][CH3:18])=[C:9]([C:8]([O:7][CH3:6])=[C:19]([Cl:22])[CH:15]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 151092,6-Dimethoxybenzoic AcidHCID 24648Sulfuryl chloride

Product 1

HCID 27747503,5-Dichloro-2,6-dimethoxybenzoic Acid

Procedure

A solution of 20 ml (0.25 mol) of sulphuryl chloride in 50 ml of chloroform is added dropwise to a solution of 15.0 g (0.08 mol) 2,6-dimethoxybenzoic acid in 100 ml of chloroform. The solution is left over night at room temperature and is then refluxed for 0.5 h. The solvent is evaporated and the residue recrystallized twice from light petroleum. Yield: 17.0 g, m.p. 98°-100° C. (first recrystallization). Yield: 12.0 g, m.p. 102°-103° C. (second recrystallization).

Workup

  1. waitThe solution is left over night at room temperature
  2. temperatureis then refluxed for 0.5 h
  3. customThe solvent is evaporated
  4. customthe residue recrystallized twice from light petroleum
  5. customYield: 17.0 g, m.p. 98°-100° C. (first recrystallization)
  6. customYield: 12.0 g, m.p. 102°-103° C. (second recrystallization)

Sources & evidence

ORD record
ord-d793655f80324e32b5c6fdf764de3020
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Linked notes

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