Thionyl Chloride → Acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester

HRID 2288250Notes

Reaction equation

HRID 2288250 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:19])[C:14]=1[O:15][C:16](=[O:18])[CH3:17])[C:9](O)=[O:10]>>[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:19])[C:14]=1[O:15][C:16](=[O:18])[CH3:17])[C:9]([Cl:3])=[O:10]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 187041893,5-Dimethyl-4-acetoxybenzoic acid

Product 1

HCID 18704177Acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester

Procedure

To 21 ml of thionyl chloride was suspended 9.3 g/45 mmol of 3,5-dimethyl-4-acetoxybenzoic acid, and the suspension was refluxed under heat for 90 minutes. After cooling to room temperature, excessive thionyl chloride was distilled off under reduced pressure to obtain 9.9 g of the desired 3,5-dimethyl-4-acetoxybenzoyl chloride.

Workup

  1. temperaturethe suspension was refluxed
  2. temperatureunder heat for 90 minutes
  3. distillationexcessive thionyl chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-16559980dd7148ee876631cd020ae77f
Source dataset
uspto-grants-2000_07
Patent number
US06087502

Reaction notes

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