4-Formylbenzoic acid → 4-Formylbenzoyl chloride

HRID 1844816Notes

Reaction equation

HRID 1844816 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-9e7d803bfed749c18e09c3a9fa59e6ee
Source dataset
uspto-grants-2015_02
Patent number
US08946492B2

Reaction notes

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