2-Benzoylbenzoic Acid → 3-chloro-3-phenyl-1-(3H)-isobenzofuranone

HRID 2164609Notes

Reaction equation

HRID 2164609 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>>[Cl:20][C:1]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=[O:13])[O:12]1

Participants

3

Reactant 2

HCID 68132-Benzoylbenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 35605513-chloro-3-phenyl-1-(3H)-isobenzofuranone

Procedure

Over a period of 15 minutes, 22.5 parts of 2-benzoylbenzoic acid are added, in small portions, while stirring, to 40 parts of thionyl chloride. The reaction mixture is then brought slowly to reflux and this is maintained for 90 minutes. The excess thionyl chloride is removed in vacuo and the residue is taken up in 50 parts of anhydrous benzene and the whole is then evaporated to dryness in vacuo. The operation is repeated a second time and then the residue is taken up in 80 parts of anhydrous tetrahydrofuran. This solution is used in that form in the stage described below.

Workup

  1. temperatureto reflux
  2. temperaturethis is maintained for 90 minutes
  3. customThe excess thionyl chloride is removed in vacuo
  4. customthe whole is then evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-72bb1adb0a6c4fd4b7ceecdc7bb30243
Source dataset
uspto-grants-1985_03
Patent number
US04505921

Reaction notes

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