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

HRID 1606736Notes

Reaction equation

HRID 1606736 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-b0f1870ddd0143029380666428051d12
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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