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

HRID 2212329Notes

Reaction equation

HRID 2212329 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5](O)=[O:6].S(Cl)([Cl:14])=O>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([Cl:14])=[O:6]

Participants

4

Reactant 2

HCID 103563,5-Dimethylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 810883,5-Dimethylbenzoyl Chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-Dimethylbenzoic acid (25 g, 0.17 mol) and N,N-dimethylformamide (0.1 mL) were added to thionyl chloride (50 mL) at 0° C. The mixture was heated to reflux for 2 hours. The excess thionyl chloride was distilled off under reduced pressure and toluene (50 mL) was added to the residue. Toluene was distilled off under reduced pressure to obtain oily 3,5-dimethylbenzoyl chloride. A solution of propyleneimine (14 mL, 0.18 mol) in tetrahydrofuran (160 mL) was added to 1N aqueous sodium hydroxide (180 mL). To the solution was added dropwise 3,5-dimethylbenzoyl chloride at 0° C. After complete addition, the mixture was further stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off to obtain 31 g of the title compound (0.16 mol, yield 99%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. distillationThe excess thionyl chloride was distilled off under reduced pressure and toluene (50 mL)
  4. additionwas added to the residue
  5. distillationToluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e156e37b6a1e48de90b5c34a09c6adf8
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

Loading…