Thionyl Chloride → 2,3,4,5-Tetramethylbenzoyl chloride

HRID 2396413Notes

Reaction equation

HRID 2396413 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>CN(C)C=O.C(Cl)Cl>[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([CH3:13])=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 1376292,3,4,5-Tetramethylbenzoic acid

Product 1

HCID 189870142,3,4,5-Tetramethylbenzoyl chlorideYield 142.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 3 L 3-necked flask is equipped with a condenser, argon inlet, thermowell, magnetic stirrer. The flask is purged with argon then charged with 2,3,4,5-tetramethylbenzoic acid (138.3 g, 0.776 mol), methylene chloride (1.5 L), thionyl chloride (73.5 mL, 1.01 mol) and N, N-dimethylformamide (2.0 mL, 0.026 mol). The resulting suspension is heated to reflux, after a clear solution is formed, heating is continued for 3.5 hours. The solution is allowed to cool then concentrated in vacuo. Last traces of thionyl chloride are removed by co-distillation with toluene (2×100 mL). The remaining oil is dried under high vacuum then used without further purification. Additional reactions are carded out to produce a total of 218 g of 2,3,4,5-tetramethylbenzoyl chloride.

Workup

  1. customA 3 L 3-necked flask is equipped with a condenser, argon inlet
  2. customThe flask is purged with argon
  3. temperatureThe resulting suspension is heated
  4. temperatureto reflux
  5. customafter a clear solution is formed
  6. temperatureheating
  7. temperatureto cool
  8. concentrationthen concentrated in vacuo
  9. customLast traces of thionyl chloride are removed by co-distillation with toluene (2×100 mL)
  10. customThe remaining oil is dried under high vacuum
  11. customthen used without further purification

Sources & evidence

ORD record
ord-9fefe5e8388b4a6f8d950cf31d003804
Source dataset
uspto-grants-1996_02
Patent number
US05492690

Reaction notes

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