8-fluorooctanoic acid synthesis
- Product Name:8-fluorooctanoic acid
- CAS Number:353-25-3
- Molecular formula:C8H15FO2
- Molecular Weight:162.2
616205-77-7
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Yield:353-25-3 95%
Reaction Conditions:
with lithium hydroxide monohydrate in methanol;water;Inert atmosphere;
Steps:
8-Fluorooctanoic acid (9).
To a solution of 13 (360 mg, 2.05 mmol) stirring in 3:1 MeOH:H2O (12 mL) was added LiOH·H2O(430 mg, 6.15 mmol). The mixture was stirred overnight. Upon completion of the reaction, methanol was first removed under reduced pressure. The reaction mixture was diluted with ethyl acetate, then acidified with 1N HCl. The two layers were separated, and the aqueous layer was extracted with ethyl acetate.The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to afford 9 as a colorless oil. Rf = 0.45 (3:1 hexanes/ethylacetate). 1H NMR (600 MHz, CDCl3) δ 4.38 - 4.49 (dt, J = 47.42, 6.13 Hz, 2H), 2.34 - 2.37 (t,J = 7.59 Hz, 2H), 1.62 - 1.74 (m,4H), 1.35 - 1.43 (m, 6H). 13C NMR (150 MHz, CDCl3) δ 179.0,84.9, 83.8, 34.0, 30.6, 30.5, 29.1, 25.2, 24.8. 19F NMR (565 MHz, CDCl3) δ -218.16.
References:
Kim, Eliana E.;Onyango, Evans O.;Fu, Liangfeng;Gribble, Gordon W. [Tetrahedron Letters,2015,vol. 56,# 48,p. 6707 - 6710] Location in patent:supporting information
408-27-5
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![Octanoic acid, 8-[[(4-methylphenyl)sulfonyl]oxy]-, ethyl ester](/CAS/20210305/GIF/144682-03-1.gif)
144682-03-1
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353-25-3
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