Sodium Iodide → Allyl 3-iodomethylbenzoate

HRID 2414369Notes

Reaction equation

HRID 2414369 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7].[I-:15].[Na+]>CC(C)=O>[I:15][CH2:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 114243703-Chloromethyl-benzoic acid allyl ester

Product 1

HCID 11808802Allyl 3-iodomethylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of allyl 3-(chloromethyl)-benzoate (54.5 g, 0.259 mmol) and sodium iodide (46.56 g, 0.311 mol) in acetone (500 mL) is stirred at room temp. for 6.5 hours, after which time the mixture is filtered. The filtrate is evaporated and the residue is dissolved in diethyl ether (500 mL), then washed with water (1×200 mL), 5% sodium sulfite solution (1×200 mL) and brine (1×200 mL), dried over magnesium sulfate, and evaporated to yield allyl 3-(iodomethyl)-benzoate as a white solid.

Workup

  1. filtrationafter which time the mixture is filtered
  2. customThe filtrate is evaporated
  3. dissolutionthe residue is dissolved in diethyl ether (500 mL)
  4. washwashed with water (1×200 mL), 5% sodium sulfite solution (1×200 mL) and brine (1×200 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-91719192555342d1abd3465f6b7c319f
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

Loading…