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Finkelstein Reaction of 3-Chloro-1-Propanol with Sodium Iodide; 3-Iodo-1-Propanol

SyntheticPage 551
DOI: 10.1039/SP551
Submitted Mar 30, 2012, published Apr 06, 2012
Christopher Kelly (christopher.b.kelly@uconn.edu)
A contribution from Leadbeater Group


			Reaction Scheme: <IMG src="/images/empty.gif">Finkelstein Reaction&nbsp;of <SPAN id=csm1378729946201 class=csm-chemical-name title=3-Chloro-1-Propanol grpid="1">3-Chloro-1-Propanol</SPAN> with Sodium Iodide<IMG src="/images/empty.gif">

Chemicals Used

3-Chloro-1-Propanol (98% Purity, Sigma Aldrich)
Acetone (CHROMASOLV®, for HPLC, ≥99.9%, Sigma Aldrich)
Sodium Iodide (ACS reagent, ≥99.5%, Sigma Aldrich)
Diethyl Ether (anhydrous, ≥99.7%, 1 ppm BHT, Sigma Aldrich)
Hexanes (mixture of isomers, anhydrous, ≥99%, Purchased from Sigma Aldrich)
Sodium thiosulfate (ReagentPlus®, 99%)
Sodium Sulfate (ACS reagent, ≥99.0%, anhydrous, granular)

Procedure

To a 100 mL flask equipped a large stir bar was added the 3-chloro-1-propanol (4.73 g, 0.050 mol) and acetone (50 mL, 1 M in the alcohol). Sodium iodide (37.47 g, 0.250 mol) was then added all at once to the flask . The flask was then equipped with a reflux condenser and, after placing the reaction under a nitrogen atmosphere, was heated to reflux. The mixture was allowed to react for 24 hours. After this time, the now yellow solution was filtered through a medium porosity fritted funnel, eluting with ≈200 mL of acetone into a 500 mL round-bottom flask.1 The solvent was removed by rotary evaporation to afford a dry orange solid. This solid was triturated with a 1:1 v./v. hexanes to Et2O solution  (2 X 200mL) and the grey fine precipitate was removed by filtration through a medium porosity fritted funnel.2  The slightly clouded3 yellow-tinged filtrate was washed with ≈100 mL of a 10% w./w. sodium thiosulfate solution, causing the organic layer to become colorless. The organic layer was then washed with ≈100 mL of deionized water, followed by ≈100 mL of brine, and dried with sodium sulfate. The solvent was removed by rotary evaporation to afford pure 3-iodo-1-propanol as a pale yellow oil (7.78 g, 84%).   

Author's Comments

 1, Note that during this time the excess sodium iodide began to precipitate out as a bright orange solid. By rinsing with excess acetone, any trapped product is released into the flask, improving yield.
2. A spatula was used to break up any large orange aggregates 
3. This cloudiness if likely some residual sodium iodide which is removed during washing

Data

1H NMR (400 MHz, CDCl3) δ ppm 1.71 (s, 1 H) 2.03 (quin, J=6.30 Hz, 2 H) 3.29 (t, J=6.72 Hz, 2 H) 3.73 (t, J=5.87 Hz, 2 H)

13C NMR (100 MHz, CDCl3) δ ppm 3.25 (-CH2-I) 35.84 (-CH2-) 62.59 (-CH2-OH) 

Lead Reference

Darwish, T. A.; James, M.; Triani, G.; Hanley, T.L.; Evans, R.A.; Malic, N. J.  Am. Chem. Soc.,  2010 ,  132,  10748.

Supplementary Information

13C NMR (Iodopropanol C13NMR.jpg)
1H NMR (Iodopropanol HNMR.jpg)

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Keywords: alcohols, Alkanes, Alkyl Iodides, Halogens, nucleophilic, substitution

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