Sodium Iodide → 1-Iodoethyl 2-acetoxybenzoate

HRID 85365

Reaction equation

HRID 85365 reaction equation
CC1[O:7][CH:6]([CH3:8])[O:5][CH:4]([CH3:9])O1.[Na+].[I-:11].[C:12]([O:15][C:16]1C=[CH:20][CH:19]=[CH:18][C:17]=1C(Cl)=O)(=[O:14])[CH3:13]>C(Cl)Cl>[C:12]([O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:8]=1[C:6]([O:5][CH:4]([I:11])[CH3:9])=[O:7])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 31264ParaldehydeHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 591932991-Iodoethyl 2-acetoxybenzoateYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2,4,6-trimethyl-1,3,5-trioxane (245 mg, 1.85 mmol) and NaI (0.972 g, 6.48 mmol) in DCM (15 mL) was added a solution of 2-(chlorocarbonyl)-phenyl acetate in DCM (5 mL, 0° C.). The resulting mixture was allowed to stir (RT, 16 h). The mixture was filtrated and concentrated under reduced pressure. The crude was purified by silica gel chromatography (EtOAc-PE, 0-10%) to afford 1-iodoethyl 2-acetoxybenzoate (0.75 g, 40%) as a light yellow oil.

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated under reduced pressure
  3. customThe crude was purified by silica gel chromatography (EtOAc-PE, 0-10%)

Sources & evidence

ORD record
ord-72a7ffef402a44e3a4b4c7489ec3f10c
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Linked notes

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