2,6-Dimethylbenzoic acid → 2,6-Dimethylbenzoyl chloride

HRID 222392Notes

Reaction equation

HRID 222392 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([Cl:14])=[O:5]

Participants

4

Reactant 2

HCID 124392,6-Dimethylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 890962,6-Dimethylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 2,6-dimethylbenzoic acid (3 g; 0.02 mol) in toluene (50 ml) was added thionyl chloride (3.6 ml; 0.05 mol). The mixture thus obtained was refluxed for 2 hours. The solvent and the excess thionyl chloride were then evaporated off under reduced pressure. The residue thus obtained was taken up in toluene (50 ml) three times and evaporated under reduced pressure. The product thus obtained (3.6 g) was used without further purification.

Workup

  1. customThe mixture thus obtained
  2. temperaturewas refluxed for 2 hours
  3. customThe solvent and the excess thionyl chloride were then evaporated off under reduced pressure
  4. customThe residue thus obtained
  5. customevaporated under reduced pressure
  6. customThe product thus obtained (3.6 g)
  7. customwas used without further purification

Sources & evidence

ORD record
ord-396b2865b8034330a6403c08a42ebb9e
Source dataset
uspto-grants-2012_06
Patent number
US08207214B2

Reaction notes

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