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Sodium Iodide → 1-Iodoethyl isopropyl carbonate

HRID 537332
Notes
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Reaction equation

HRID 537332 reaction equation
[I-:1].[Na+].[C:3](=[O:12])([O:8][CH:9]([CH3:11])[CH3:10])[O:4][CH2:5][CH2:6]Cl>C(#N)C>[C:3](=[O:12])([O:8][CH:9]([CH3:11])[CH3:10])[O:4][CH:5]([I:1])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 1

HCID 110106451-Iodoethyl isopropyl carbonateYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Sodium iodide (20.69 g, 138.0 mmol) was added to the crude solution of chloroethyl isopropyl carbonate (5.11 g, 30.67 mmol) in acetonitrile (50 mL). The resulting mixture was heated to 60° C. for 2 hours and then allowed to cool to 25° C. The reaction mixture was concentrated under reduced pressure and the resulting mixture was treated with diethyl ether. The solids were filtered off and the filtrate was concentrated under reduced pressure to obtain 1-iodoethyl isopropyl carbonate as a dark orange oil (5.43 g, 69% yield).

Workup

  1. temperatureto cool to 25° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe resulting mixture was treated with diethyl ether
  4. filtrationThe solids were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38d3a8e5f0a74ecd9e034c3416016ffb
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859781B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes