4-Formylbenzoic acid → 4-Formylbenzoyl chloride

HRID 910357Notes

Reaction equation

HRID 910357 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)=[O:2].S(Cl)([Cl:14])=O>C1C=CC=CC=1.CN(C)C=O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 2

HCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 124246204-Formylbenzoyl chlorideYield 101.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

In a suspension of 1.00 g of 4-formyl benzoic acid in 15 ml of benzene, 0.87 g of thionyl chloride and 2 drops of N,N-dimethylformamide were added, and stirred under reflux with heat for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain 1.14 g of crude 4-formyl benzoic acid chloride as white crystal. In a solution of 0.66 g of 2,2,2-trifluoroethylamine and 0.81 g of triethylamine in 6 ml of chlororform, the solution of 1.14 g of the crude 4-formyl benzoic acid chloride in 6 ml of chloroform was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at room temperature for further 18 hours. After the completion of the reaction, the reaction mixture was added in 30 ml of water, extracted with chloroform (20 ml×3). The organic phase was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, the residual solid was washed with hexane to obtain 1.32 g of the aimed product as white crystal.

Workup

  1. additionwere added
  2. temperatureunder reflux
  3. temperaturewith heat for 2 hours
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-17bf32ecca4e4095abea0255f562a08c
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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