ChemicalBook CAS DataBase List 5-iodo-1-pentanol acetate

5-iodo-1-pentanol acetate synthesis

6synthesis methods

Product Name:5-iodo-1-pentanol acetate
CAS Number:65921-65-5
Molecular formula:C7H13IO2
Molecular Weight:256.08

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Yield:65921-65-5 9.47 g (100%)

Reaction Conditions:

with sodium iodide in acetone;

Steps:

1 5-Iodopentyl acetate

5-Iodopentyl acetate 5-Chloropentyl acetate (26.5 g, 0.16 mol) was added to a solution of sodium iodide (45 g, 0.30 mol) in dry acetone (200 ml). The resulting pale yellow solution was heated at reflux for 65 h, during which time a white solid separated (sodium chloride). The final mixture was cooled to room temperature and filtered to remove the NaCl, which was washed with acetone and diethyl ether, then dried under vacuum at 50° C. Expected yield of NaCl=9.4 g; isolated yield=9.47 g (100%). The filtrate and washings were combined and the solvent removed under reduced pressure; the residue was partitioned between water and diethyl ether. The ether layer was retained, washed with aqueous sodium thiosulphate solution and brine, then dried (Na₂ SO₄), filtered and the solvent removed under reduced pressure, to give titled compound as a yellow-tinged liquid, 39 g (95%). δ_H (270 MHz, CDCl₃) 1.50 (2H, m), 1.65 (2H, m), 1.85 (2H, m), 2.05 (3H, s, CH₃ --COO--), 3.18 (2H, t, I--CH₂ --), 4.06 (2H, t, --CH₂ --OAc).

References:

US6140494,2000,A

142-68-7 Synthesis