Hydrochloric Acid → p-Acetoxybenzoyl chloride

HRID 488030Notes

Reaction equation

HRID 488030 reaction equation
S(Cl)(Cl)=O.[ClH:5].S(=O)=O.[C:9]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)(=[O:11])[CH3:10]>CN(C)C=O>[C:9]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([Cl:5])=[O:18])=[CH:15][CH:14]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1119Sulfur Dioxide2×HCID 16865Benzoic acid, 4-(acetyloxy)-2×HCID 24386Thionyl Chloride

Product 1

HCID 2756254p-Acetoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

P-acetoxy benzoic acid 180.16 g (1.0 mol) was added to thionylchloride 500 ml, and dimethylformamide (DMF) 1 ml was dropped in as a catalyst and stirred, and when generation of hydrogen chloride and sulfur dioxide stopped and the reaction liquid cleared, p-acetoxy benzoic acid 180.16 g (1.0 mol) was added another 5 times, i.e. a total of 6.0 mol was added. After all 6.0 mol of the p-acetoxy benzoic acid was added and when the generation of hydrogen chloride and sulfur dioxide stopped, and the reaction liquid cleared, it was heated at reflux for 3 hours, then it was distilled and purified (at 173° C., 10 mmHg).

Workup

  1. additionwas dropped in as a catalyst
  2. customthe reaction liquid
  3. additionwas added
  4. customthe reaction liquid
  5. temperatureit was heated
  6. temperatureat reflux for 3 hours
  7. distillationit was distilled
  8. custompurified (at 173° C., 10 mmHg)

Sources & evidence

ORD record
ord-2a6e13d432d94b4399fd5f94530f73fc
Source dataset
uspto-grants-1994_03
Patent number
US05298593

Reaction notes

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