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

HRID 436173Notes

Reaction equation

HRID 436173 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](O)(O)(=O)=[O:19].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>O.C(O)(=O)C>[C:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=[O:17])(=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 24425Chromic AcidHCID 124221104-Benzyl indan-1-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 100 ml. of acetic acid is dissolved 11.1 g. of 4-benzyl indan-1-one, followed by the addition of 13.4 g. of chromic acid and 2.5 ml. of concentrated sulfuric acid. The mixture is stirred at room temperature for 2 hours, after which it is poured into 4 l. of water. After 200 g. of anhydrous potassium carbonate is added, the mixture is extracted with chloroform. The organic layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure and the oily residue is purified by column chromatography on silica gel with chloroform as the eluent and, then, recrystallized from cyclohexane. The procedure gives 4-benzoylindan-1-one melting at 87°-89° C.

Workup

  1. additionafter which it is poured into 4 l
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe oily residue is purified by column chromatography on silica gel with chloroform as the eluent
  7. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-a991f76924b343dd9dd3f97cf862a63a
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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