Dimethylformamide → (3-(Chlorocarbonyl)-2-methylphenyl)acetate

HRID 395906Notes

Reaction equation

HRID 395906 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:17])=O.CN(C)C=O>COC(C)(C)C>[C:1]([O:4][C:5]1[C:6]([CH3:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([Cl:17])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 37985573-Acetoxy-2-methylbenzoic acid

Product 1

HCID 7010345(3-(Chlorocarbonyl)-2-methylphenyl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

3-Acetoxy-2-methylbenzoic acid was slurried in methyl-t-butyl ether (MTBE) and treated with 1.2 equivalents of thionyl chloride and catalytic dimethylformamide. After three hours at ambient temperatures, the reaction was complete, giving a brown soluton. Solvent (MTBE) was removed by vacuum distillation. Residual thionyl chloride was removed by addition of toluene followed by vacuum distillation. The resulting 3-acetoxy-2-methylbenzoyl chloride was isolated either directly as an oil or by crystallization from two volumes of heptane at <10° C. Product was obtained in >100% yield when isolated as an oil and 82-85% yield when crystallized from heptane.

Workup

  1. customgiving a brown soluton
  2. customSolvent (MTBE) was removed by vacuum distillation
  3. customResidual thionyl chloride was removed by addition of toluene
  4. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-3e683167b7604366a58efde2e0b51d76
Source dataset
uspto-grants-2003_08
Patent number
US06605721B2

Reaction notes

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