4-Chlorophenol → 2-[8-(4-Chlorophenoxy)octyl]-4,5,6,7-tetramethoxyindan

HRID 2268480Notes

Reaction equation

HRID 2268480 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[C:13]([O:25][CH3:26])[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]=2[O:19][CH3:20])[CH2:11]1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]2[CH2:18][C:17]3[C:12](=[C:13]([O:25][CH3:26])[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]=3[O:19][CH3:20])[CH2:11]2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 183485412-(8-Iodooctyl)-4,5,6,7-tetramethoxyindan

Product 1

HCID 183485992-[8-(4-Chlorophenoxy)octyl]-4,5,6,7-tetramethoxyindanYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of 2-(8-iodooctyl)-4,5,6,7-tetramethoxyindan (830 mg), 4-chlorophenol (269 mg), and potassium carbonate (481 mg) in DMF (8 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=10:1) to yield the entitled compound (776 mg) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-de9cf7cf7fb24cd9acc41f503b16b71d
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…