Hydrochloric Acid → 4-Benzoyl-2,3-dihydro-1H-inden-1-one

HRID 1763432Notes

Reaction equation

HRID 1763432 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH2:4][CH2:3]1.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2=[O:1])(=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 6451240Aluminum(III) ChlorideHCID 125422061-Oxo-indan-4-carboxylic acid

Product 1

HCID 131930944-Benzoyl-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 100 ml. of dry benzene are added 17.6 g. of 1-oxoindan-4-carboxylic acid and 22.9 g. of phosphorus pentachloride and, after stirring for 1.5 hours, 40 g. of aluminum chloride is added. The mixture is stirred for 5 hours, after which the product is poured into dilute hydrochloric acid and extracted with ether. The organic layer is dried and distilled free of the solvent under reduced pressure. The crystalline residue is recrystallized from cyclohexane. The described procedure gives 4-benzoylindan-1-one which melts at 87°-89° C.

Workup

  1. extractionextracted with ether
  2. customThe organic layer is dried
  3. distillationdistilled free of the solvent under reduced pressure
  4. customThe crystalline residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-dc77c5d53731423fb30194efcdc36371
Source dataset
uspto-grants-1978_09
Patent number
US04111997

Reaction notes

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