Thionyl Chloride → 2-Chloro-6-methylbenzoyl chloride

HRID 1047802Notes

Reaction equation

HRID 1047802 reaction equation
[Cl: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>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([Cl:14])=[O:5]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 888702-Chloro-6-methylbenzoic acid

Product 1

HCID 223820402-Chloro-6-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A round bottom flask containing the 2-chloro-6-methyl-benzoic acid (1.5 g, 8.79 mmol) and a stirring bar is charged with dry DCM (10 mL). Stirring is initiated. After several min, a solution of thionyl chloride (in DCM (2M), 6.6 mL, 13.2 mmol) is added via syringe. 2 drops of DMF are then added. The reaction immediately began to bubble gently. After 2 h bubbling ceases. After 3 h, the solvent is removed from the reaction mixture in vacuo. The oily residue is redissolved in DCM (6 mL) and the solvent once again removed in vacuo. The residue is dissolved in dry DCM (6 mL) and used without further purification in the next reaction sequence.

Workup

  1. customThe reaction
  2. customto bubble gently
  3. customAfter 2 h bubbling ceases
  4. customthe solvent is removed from the reaction mixture in vacuo
  5. dissolutionThe oily residue is redissolved in DCM (6 mL)
  6. customthe solvent once again removed in vacuo
  7. dissolutionThe residue is dissolved in dry DCM (6 mL)
  8. customused without further purification in the next reaction sequence

Sources & evidence

ORD record
ord-3c4cd1774eef4f80902b52bf181d53b2
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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