Sulfuric Acid → (4-Methoxyphenyl)(3-phenyl-1H-inden-2-yl)methanone

HRID 1872097Notes

Reaction equation

HRID 1872097 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(=O)(=O)(O)O>CCOCC.C1C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([C:3]2[CH2:4][C:5]3[C:10]([C:2]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 12272538HCID 12272538, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 18690194(4-Methoxyphenyl)(3-phenyl-1H-inden-2-yl)methanoneYield 57%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A slurry of 13.25 g (50 mmol) of 1-oxo-2-(4-methoxybenzoyl)indane in a mixture of 300 mL of ether and 300 mL of benzene was prepared. To the slurry was added 35.66 g (197 mmol) of phenylmagnesium bromide. The resulting mixture was heated to reflux for sixteen hours and poured into a mixture of ice and sulfuric acid. The mixture was allowed to separate and the organic layer was removed. The organic extract was washed with a bicarbonate solution, dried over sodium sulfate, filtered, and concentrated to a red oil. A small amount of ether was added to the oil and a crystalline precipitate formed. The crystals were removed by filtration. The filtrate was concentrated to dryness and the product crystallized from methanol to yield 9.3 g of the title compound.

Workup

  1. customwas prepared
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for sixteen hours
  4. customto separate
  5. customthe organic layer was removed
  6. extractionThe organic extract
  7. washwas washed with a bicarbonate solution
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a red oil
  11. additionA small amount of ether was added to the oil
  12. customa crystalline precipitate formed
  13. customThe crystals were removed by filtration
  14. concentrationThe filtrate was concentrated to dryness
  15. customthe product crystallized from methanol

Sources & evidence

ORD record
ord-2e7cdb04102d469da094e690a993fe73
Source dataset
uspto-grants-2000_08
Patent number
US06107346

Reaction notes

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