Sodium Chloride → 4-Benzoyl-2,3-dihydro-1H-inden-1-one

HRID 1606718Notes

Reaction equation

HRID 1606718 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([OH:19])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>O>[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:10]=1[CH2:15][CH2:16][C:17]2=[O:19])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 12286997Benzenepropanoic acid, 2-benzoyl-

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Five g. of o-benzoyl-β-phenylpropionic acid, 13 g. of anhydrous aluminum chloride and 1.3 g. of sodium chloride are admixed together and heated at 160°C for 1 hour. After cooling, water is added to the mixture, followed by extraction with chloroform. The extract is washed with a 5 % aqueous solution of sodium bicarbonate and water in that order and, then, dried. The solvent is distilled off under reduced pressure and the residue is dissolved in ethanol. The solution is decolorized with activated carbon and recrystallized from ethanol. The procedure yields 4-benzoylindan-1-one as crystals melting at 86°-88°C.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with chloroform
  3. washThe extract is washed with a 5 % aqueous solution of sodium bicarbonate and water in that order
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure
  6. dissolutionthe residue is dissolved in ethanol
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3e617f3e9cc742f38adf3420db637316
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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