Thionyl Chloride → 2,3-Dichloro-4-methylbenzoyl chloride

HRID 1889020Notes

Reaction equation

HRID 1889020 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 534304632,3-Dichloro-4-methylbenzoic acid

Product 1

HCID 866667402,3-Dichloro-4-methylbenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-Dichloro-4-methylbenzoic acid (I70) (5.90 g, 26.2 mmol) and thionyl chloride (30 mL, 411 mmol) were heated at 85° C. for 4 hr in toluene (100 mL). The solvents were removed in vacuo and the residue was azeotroped with toluene (3×100 mL). The residue was used in subsequent steps without further purification assuming 100% yield. Compound not characterised at this step.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was azeotroped with toluene (3×100 mL)
  3. customThe residue was used in subsequent steps without further purification

Sources & evidence

ORD record
ord-0b4f10b90a43412d8a4e0eb289a0de2d
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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