2,6-Dimethoxybenzoic Acid → 3-Chloro-2,6-dimethoxybenzoic acid

HRID 224417

Reaction equation

HRID 224417 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:9]=1[C:10]([OH:12])=[O:11]>C(Cl)(Cl)Cl>[Cl:4][C:16]1[C:8]([O:7][CH3:6])=[C:9]([C:13]([O:17][CH3:18])=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 151092,6-Dimethoxybenzoic AcidHCID 24648Sulfuryl chloride

Product 1

HCID 6121993-Chloro-2,6-dimethoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 16.2 ml (0.2 mol) of sulphuryl chloride in 100 ml of chloroform is added dropwise while stirring to a solution of 36.4 g (0.2 mol) of 2,6-dimethoxybenzoic acid in 300 ml of chloroform. The mixture is heated for 0.5 h at 50° C. and left overnight at room temperature. The solvent is evaporated and the residue recrystallized from isopropyl ether--light petroleum. Yield: 35.4 g, m.p. 132°-33° C.

Workup

  1. customThe solvent is evaporated
  2. customthe residue recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-71ed333a1fb041258c5bd0fea60222fc
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Linked notes

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