Sodium Iodide → HCID 22759268, compound

HRID 1730123Notes

Reaction equation

HRID 1730123 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH:15]([O:25][C:26](=[O:28])[CH3:27])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)(C1C=CC(C)=CC=1)(=O)=O.[I-:29].[Na+]>CC(C)=O>[C:26]([O:25][CH:15]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH2:14][CH2:13][CH2:12][I:29])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 53925496HCID 53925496, compound

Product 1

HCID 22759268HCID 22759268, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-acetoxy-5-(4-fluorophenoxy)- 1-pentanol tosylate (73.5 g., 0.179 mole) and sodium iodide (79.5 g., 0.53 mole) in acetone (500 ml.) is allowed to stand at 25°-27° for 18 hours. The precipitated sodium tosylate is filtered off. Most of the acetone is evaporated from the filtrate and the residue is treated with 300 ml. of water. The oily product is taken up in ether, washed with dilute sodium thiosulfate solution, water and brine and dried over sodium sulfate. The solvent is distilled in vacuo to give 66 g. (a quantitative yield) of the crude title compound as a yellowish oil which is used without further purification; pmr (CDCl3) δ 2.05 (3H, s CH3CO); 3.20 (2H, t CH2I); 3.97 (2H, d CH2O); 5.20 (1H, m CHO); 6.85 (4H, m aryl).

Workup

  1. filtrationThe precipitated sodium tosylate is filtered off
  2. customMost of the acetone is evaporated from the filtrate
  3. additionthe residue is treated with 300 ml
  4. washwashed with dilute sodium thiosulfate solution, water and brine
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent is distilled in vacuo
  7. customto give 66 g
  8. custom(a quantitative yield) of the crude title compound as a yellowish oil which is used without further purification

Sources & evidence

ORD record
ord-8beff584fa0c473bb0047ed8aab9d7a1
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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