Sodium Iodide → Isopropoxycarbonyloxyethyl iodide

HRID 248211Notes

Reaction equation

HRID 248211 reaction equation
[CH:1]([O:4][C:5]([O:7][CH2:8][CH2:9]Cl)=[O:6])([CH3:3])[CH3:2].[I-:11].[Na+]>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)(Cl)Cl>[CH:1]([O:4][C:5]([O:7][CH2:8][CH2:9][I:11])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 197651192-Chloroethyl propan-2-yl carbonate

Product 1

HCID 19765127Isopropoxycarbonyloxyethyl iodideYield 57.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of isopropoxycarbonyloxyethyl chloride (=2-chloroethyl isopropylcarbonate) (1.67 g), carbon tetrachloride (10 ml), sodium iodide (2.10 g) and anhydrous zinc chloride (0.08 g) is stirred at room temperature for 2 hours, and thereafter, ice water is added to the mixture. The organic layer is separated, and the aqueous layer is extracted twice.with carbon tetrachloride. The combined organic layers are washed, dried and evaporated under reduced pressure to give isopropoxycarbonyloxyethyl iodide (=2-iodoethyl isopropylcarbonate) (1.48 g) as an oil.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted twice.with carbon tetrachloride
  3. washThe combined organic layers are washed
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-89e5832df91a4a02a5a9d6bf1742368b
Source dataset
uspto-grants-1993_05
Patent number
US05208348

Reaction notes

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