Sodium Iodide → Allyl 3-iodomethylbenzoate

HRID 276721Notes

Reaction equation

HRID 276721 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 filitrate 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, which was is directly.

Workup

  1. filtrationafter which time the mixture is filtered
  2. customThe filitrate 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-4e13bb20fb0d480bbd27e73122f5425f
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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