Hydrochloric Acid → 4-(p-Chlorobenzoyl)indan-1-one

HRID 436168Notes

Reaction equation

HRID 436168 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-:20].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1>[Cl:20][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH2:4][CH2:3][C:2]3=[O:1])=[O:13])=[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 131930974-(p-Chlorobenzoyl)indan-1-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 200 ml. of chlorobenzene are added 17.6 g. of 1-oxoindan-4-carboxylic acid and 23 g. of phosphorus pentachloride. The mixture is stirred at room temperature for 3 hours, after which time 40 g. of aluminum chloride is added. The mixture is stirred at about 65° C for 3 hours. After cooling, the mixture is poured into ice and hydrochloric acid, followed by extraction with chloroform. The extract is washed with water, a saturated aqueous solution of sodium bicarbonate and water in the order mentioned. After drying, the solvent is distilled off under reduced pressure and the residue is purified by column chromatography on silica gel (200 g. silica gel; eluted with chloroform). Finally, recrystallization from a 20:5 mixture of benzene and hexane gives 4-(p-chlorobenzoyl)indan-1-one as crystals melting at 144.5°-146° C.

Workup

  1. stirringThe mixture is stirred at about 65° C for 3 hours
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with chloroform
  4. washThe extract is washed with water
  5. customAfter drying
  6. distillationthe solvent is distilled off under reduced pressure
  7. customthe residue is purified by column chromatography on silica gel (200 g. silica gel; eluted with chloroform)
  8. customFinally, recrystallization
  9. additionfrom a 20:5 mixture of benzene and hexane

Sources & evidence

ORD record
ord-fc43a711f12c43a6970ff2b4f5ffeaae
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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