Sodium Iodide → 2,3-dihydro-2,4,6-trimethyl-7-hydroxy-2-benzyl-1H-indene-1-one

HRID 330241Notes

Reaction equation

HRID 330241 reaction equation
[CH3:1][C:2]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C:9]2[C:4](=[C:5]([O:13]C)[C:6]([CH3:12])=[CH:7][C:8]=2[CH3:11])[C:3]1=[O:15].[I-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-]>C(#N)C>[CH3:1][C:2]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C:9]2[C:4](=[C:5]([OH:13])[C:6]([CH3:12])=[CH:7][C:8]=2[CH3:11])[C:3]1=[O:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6451240Aluminum(III) ChlorideHCID 148347342,3-dihydro-2,4,6-trimethyl-7-methoxy-2-benzyl-1H-inden-1-one

Product 1

HCID 143905432,3-dihydro-2,4,6-trimethyl-7-hydroxy-2-benzyl-1H-indene-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

23.0 Grams of 2,3-dihydro-2,4,6-trimethyl-7-methoxy-2-benzyl-1H-inden-1-one and 25.8 g of sodium iodide were dissolved in 90 ml of acetonitrile. To this solution was added 22.9 g of aluminium chloride at room temperature and stirred for 1 hour. Then the solvent was removed by evaporation under a reduced pressure, and the residue thus obtained was extracted with ethyl acetate. The extract was washed with an aqueous solution saturated with sodium chloride, an aqueous solution of sodium thiosulfate and an aqueous solution saturated with sodium chloride in this order, and the insoluble matters were removed by filtration. The solvent was removed by evaporation and the residue thus obtained was recrystallized from n-hexane to obtain 19.7 g of 2,3-dihydro-2,4,6-trimethyl-7-hydroxy-2-benzyl-1H-indene-1-one. Colorless prism-like crystals. Melting point: 86°-87° C.

Workup

  1. customThen the solvent was removed by evaporation under a reduced pressure
  2. customthe residue thus obtained
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution saturated with sodium chloride
  5. customan aqueous solution of sodium thiosulfate and an aqueous solution saturated with sodium chloride in this order, and the insoluble matters were removed by filtration
  6. customThe solvent was removed by evaporation
  7. customthe residue thus obtained
  8. customwas recrystallized from n-hexane

Sources & evidence

ORD record
ord-bf878e54ce7545d082363d12bc322a3a
Source dataset
uspto-grants-1990_01
Patent number
US04895847

Reaction notes

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