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

HRID 436167Notes

Reaction equation

HRID 436167 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-ff723d77723e4d2d850295f246d483b4
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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