Sodium Iodide → 1-Iodoethyl isopropyl carbonate

HRID 1913541Notes

Reaction equation

HRID 1913541 reaction equation
[C:1](=[O:10])([O:6][CH:7]([CH3:9])[CH3:8])[O:2][CH:3](Cl)[CH3:4].[I-:11].[Na+].C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1](=[O:10])([O:6][CH:7]([CH3:9])[CH3:8])[O:2][CH:3]([I:11])[CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 2855718-Crown-6HCID 117895851-Chloroethyl 1-methylethyl carbonate

Product 1

HCID 110106451-Iodoethyl isopropyl carbonateYield 97.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-chloroethyl isopropyl carbonate (1.00 g) in toluene (30 mL), sodium iodide (2.10 g) and 18-crown-6 (185 mg) were added at room temperature, and the mixture was stirred at 100° C. for 5 hours. To the reaction solution, ethyl acetate was added, and the mixture was washed with water and 5% aqueous sodium thiosulfate in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product of the title compound (1.51 g).

Workup

  1. washthe mixture was washed with water and 5% aqueous sodium thiosulfate in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7f830fcff7e3438ab1d496091cf5f072
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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