Water → 5-Hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2308869Notes

Reaction equation

HRID 2308869 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[S:9][C:8]2[C:10]([CH3:17])=[C:11]([OH:16])[C:12]([CH3:15])=[C:13]([CH3:14])[C:7]=2[O:6]1.[I-:18].[Na+].O>CC(C)=O>[OH:16][C:11]1[C:12]([CH3:15])=[C:13]([CH3:14])[C:7]2[O:6][CH:5]([CH2:4][CH2:3][CH2:2][I:18])[S:9][C:8]=2[C:10]=1[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 148021822-(3-Chloropropyl)-5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole

Product 1

HCID 135920605-Hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

120 mg of 2-(3-chloropropyl)-5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 77) were dissolved in 2 ml of acetone, after which 660 mg of sodium iodide were added, and the reaction mixture was heated under reflux for 10 hours. The reaction mixture was cooled and then poured into water, and the resulting precipitate was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure and the resulting crude product was purified in the same manner as described in (a), to give the title compound having the same Rf value and mass spectrum as the product of (a) above.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 10 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionthe resulting precipitate was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe ethyl acetate was distilled off under reduced pressure
  8. customthe resulting crude product was purified in the same manner

Sources & evidence

ORD record
ord-759abb2ae46047f691aeebbd1effb157
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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