Sodium Iodide → HCID 5370550, compound

HRID 1702579Notes

Reaction equation

HRID 1702579 reaction equation
[Na+].[I-:2].[CH3:3][O:4]/[C:5](/[CH2:12]Cl)=[CH:6]\[C:7]([O:9][CH2:10][CH3:11])=[O:8]>CC(C)=O>[CH3:3][O:4]/[C:5](/[CH2:12][I:2])=[CH:6]\[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 14372562HCID 14372562, compound

Product 1

HCID 5370550HCID 5370550, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Fifteen grams (0.1 mol) of NaI was added to a solution of 3.58 g (0.02 mol) of ethyl 3-methoxy-4-chlorocrotonate in 150 mL of acetone. The solution was stirred vigorously for 20 h in a flask protected from light and standard workup yielded 5.38 g (100%) of ethyl 3-methoxy-4-iodocrotonate as an amber liquid: VPC (6 ft 5% SF96 on 60-80 mesh chromosorb G; 160° C.; 60 cm3 /min He flow) tR =4.0 min; NMR (CDCl3)δ1.31 (t, 3H, J=7 Hz, COOCCH3), 3.73 (s, 3H, OCH3), 4.24 (q, 2H, J=7 Hz, COOCH2C), 4.48 (s, 2H, CH2I), 5.13 (s, 1H, CH).

Sources & evidence

ORD record
ord-c3fd374efa194cd7a9fd007921e6db9d
Source dataset
uspto-grants-1982_09
Patent number
US04348333

Reaction notes

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