Sodium Iodide → HCID 20386093, compound

HRID 46975Notes

Reaction equation

HRID 46975 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH:15]([O:21][C:22](=[O:24])[CH3:23])[CH2:16][O:17][CH2:18][CH2:19][CH3:20])(C1C=CC(C)=CC=1)(=O)=O.[I-:25].[Na+]>CC(C)=O>[C:22]([O:21][CH:15]([CH2:16][O:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13][CH2:12][I:25])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 538286304-Acetoxy-5-propoxy-1-pentanol Tosylate

Product 1

HCID 20386093HCID 20386093, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-acetoxy-5-propoxy-1-pentanol tosylate (61.5 g., 0.179 mole) and sodium iodide (79.5 g., 0.53 mole) in acetone (500 ml.) is allowed to stand at 25°-27° C. 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 a quantitative yield of the crude title compound as a yellowish oil which is used without further purification.

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

Sources & evidence

ORD record
ord-409d2ca0c2dc4bde89dceec13eac2e36
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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