Thionyl Chloride → 4-(Chlorocarbonyl)phenyl benzoate

HRID 854223Notes

Reaction equation

HRID 854223 reaction equation
[C:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>CN(C)C=O>[C:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:21])=[O:15])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 119979Benzoic acid, 4-(benzoyloxy)-

Product 1

HCID 150272094-(Chlorocarbonyl)phenyl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

10.00 g (41.3 mmol) of 4-(benzoyloxy)benzoic acid and one drop of N,N-dimethylformamide are refluxed in 40 ml of thionyl chloride with stirring until gas is no longer evolved. The excess thionyl chloride is very substantially removed by distillation under reduced pressure and co-distilled twice with petroleum ether (50/70) under reduced pressure from the remaining residue for complete removal. Purification is carried out by recrystallization from 150 ml of petroleum ether (50/70)/ethyl acetate 2:1, and the crystals are washed with 4 ml of petroleum ether (50/70)

Workup

  1. customThe excess thionyl chloride is very substantially removed by distillation under reduced pressure
  2. customco-distilled twice with petroleum ether (50/70) under reduced pressure from the remaining residue for complete removal
  3. customPurification
  4. customis carried out by recrystallization from 150 ml of petroleum ether (50/70)/ethyl acetate 2:1
  5. washthe crystals are washed with 4 ml of petroleum ether (50/70)

Sources & evidence

ORD record
ord-c5bb76b319364229ad4cf68f04c53584
Source dataset
uspto-grants-2007_08
Patent number
US07258902B2

Reaction notes

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