3,5-Dimethylbenzoic acid → 3,5-Dimethylbenzoyl Chloride

HRID 1707698Notes

Reaction equation

HRID 1707698 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:9](O)=[O:10]>C1(C)C=CC=CC=1>[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:9]([Cl:3])=[O:10]

Participants

4

Reactant 2

HCID 103563,5-Dimethylbenzoic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 810883,5-Dimethylbenzoyl Chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.0 kg. (16.3 moles) of thionyl chloride is added dropwise over a period of 45 minutes to a suspension of 2.0 kg. (13.32 moles) of 3,5-dimethylbenzoic acid in 8 l. of toluene stirred at 65° C. under nitrogen during the course of which the temperature is kept below 80° C. The reaction mixture is stirred at 110°-115° C. under nitrogen for 5 hours and cooled, and the toluene and excess thionyl chloride are vacuum distilled at 55°-60° C. to obtain 2.247 kg. of crude product. A small sample is purified by vacuum distillation. B.p. 52°-57° C./0.25 mm Hg.

Workup

  1. customis kept below 80° C
  2. temperaturecooled
  3. distillationdistilled at 55°-60° C.
  4. customto obtain 2.247 kg
  5. distillationA small sample is purified by vacuum distillation

Sources & evidence

ORD record
ord-62af36d85ab149e3b95774f2ffb6f903
Source dataset
uspto-grants-1994_10
Patent number
US05354772

Reaction notes

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