Sodium Iodide → 2-Propenoic acid, 3-iodo-, 1-methylethyl ester, (2Z)-
Reaction equation
[C:1]([O:5][CH:6]([CH3:8])[CH3:7])(=[O:4])[C:2]#[CH:3].[Na+].[I-:10]>CC(O)=O>[I:10]/[CH:3]=[CH:2]\[C:1]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 115 °C
Procedure
To a mixture of isopropyl propiolate (350 g, 3.1 moles) in AcOH (1300 mL) was added NaI (930 g, 6.2 moles) at 25° C. The reaction mixture was heated to 115° C. and stirred for 1.5 hrs. The reaction mixture was cooled to 25 to 30° C. and quenched with water followed by extraction with MTBE. The organic layer was washed with saturated bicarbonate, bisulfite and brine solution. The organic layer was dried over sodium sulfate and concentrated under vacuum to give the product (Z)-isopropyl 3-iodoacrylate (626 g; 83.5%). Product was confirmed by 1H NMR.
Workup
- temperatureThe reaction mixture was cooled to 25 to 30° C.
- customquenched with water
- extractionfollowed by extraction with MTBE
- washThe organic layer was washed with saturated bicarbonate, bisulfite and brine solution
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-9e1076c336c6475db26479acde0e0baf
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206158B2
Reaction notes
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