Water → 2-(8-Iodooctyl)-4,5,6,7-tetramethoxyindan

HRID 2268473

Reaction equation

HRID 2268473 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:22][C:21]2[C:16](=[C:17]([O:29][CH3:30])[C:18]([O:27][CH3:28])=[C:19]([O:25][CH3:26])[C:20]=2[O:23][CH3:24])[CH2:15]1)(=O)=O.[I-:31].[Na+].O>CC(C)=O>[I:31][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:22][C:21]2[C:16](=[C:17]([O:29][CH3:30])[C:18]([O:27][CH3:28])=[C:19]([O:25][CH3:26])[C:20]=2[O:23][CH3:24])[CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 183485438-(4,5,6,7-Tetramethoxyindan-2-yl)octyl methanesulfonate

Product 1

HCID 183485412-(8-Iodooctyl)-4,5,6,7-tetramethoxyindanYield 96.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 8-(4,5,6,7-tetramethoxyindan-2-yl)octyl methanesulfonate (2.36 g), sodium iodide (2.38 g) in acetone (20 ml) was heated under reflux for 3 hr. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium sulfite, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (2.44 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with 5% aqueous sodium sulfite, water, and saturated aqueous sodium chloride
  5. customdried
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-12e43a8690a64c9db37601c105d348df
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Linked notes

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