2-Dimethylaminopyridine → 2,4-Dichloro-6-methyloxybenzoyl chloride

HRID 1073481Notes

Reaction equation

HRID 1073481 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[C:4](O)=[O:5].CN(C1C=CC=CN=1)C.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[C:4]([Cl:25])=[O:5]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 24386Thionyl ChlorideHCID 135533172,4-Dichloro-6-methoxybenzoic acid

Product 1

HCID 137948482,4-Dichloro-6-methyloxybenzoyl chlorideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

26.0 g. (0.117 mol) 2,4-Dichloro-6-methoxybenzoic acid were dissolved in 50 ml. anhydrous methylene chloride and, after the addition of 0.1 g. dimethylaminopyridine, 50 ml. thionyl chloride were added dropwise thereto at ambient temperature. After stirring for 15 hours, the reaction mixture was evaporated and the residue distilled. Yield: 55% of theory; b.p. 118-124° C./0.1 mm.Hg.

Workup

  1. customat ambient temperature
  2. customthe reaction mixture was evaporated
  3. distillationthe residue distilled

Sources & evidence

ORD record
ord-54c91ab192824b9c8107ede9611926c7
Source dataset
uspto-grants-1990_11
Patent number
US04970077

Reaction notes

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