Sodium Iodide → HCID 21317577, compound

HRID 2083316Notes

Reaction equation

HRID 2083316 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH:14]([O:27][C:28](=[O:30])[CH3:29])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)(=O)=O)=CC=1.[I-:32].[Na+]>CC(C)=O>[I:32][CH2:11][CH2:12][CH2:13][CH:14]([O:27][C:28](=[O:30])[CH3:29])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 213176291-(p-Toluenesulfonyloxy)-4-acetoxy-5-(3-trifluoromethylphenoxy)pentane

Product 1

HCID 21317577HCID 21317577, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-(p-toluenesulfonyloxy)-4-acetoxy-5-(3-trifluoromethylphenoxy)pentane (125 g., 0.28 mole) and sodium iodide (126 g., 0.84 mole) in acetone (600 ml.) is allowed to stand at 25°-27° for 16 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 magnesium sulfate. The solvent is distilled in vacuo to yield 113 g. (97%) of the crude title compound as a yellowish oil which is used without further purification; pmr (CDCl3) 2.06 (3H, s CH3O); 3.20 (2H, t CH2I); 4.01 (2H, d CH2O); 5.20 (1H, m CHO).

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 magnesium sulfate
  6. distillationThe solvent is distilled in vacuo
  7. customto yield 113 g
  8. custom(97%) of the crude title compound as a yellowish oil which is used without further purification

Sources & evidence

ORD record
ord-8700f8db82974e63a06c23ac937c440f
Source dataset
uspto-grants-1978_04
Patent number
US04085125

Reaction notes

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