ALLYL 1H,1H-HEPTAFLUOROBUTYL ETHER synthesis

Yield:648-42-0 69%

Reaction Conditions:

with sodium hydroxide in neat (no solvent) at 80; for 7 h;Autoclave;

Steps:

4.2.1 Synthesis of 4-(allyloxy)-1,1,1,2,2,3,3-heptafluorobutane (1)

A flask was charged with perfluorinated alcohol C₃F₇CH₂OH (40.0 g, 0.20 mol), allyl bromide (24.2 g, 0.20 mol) and grinded NaOH (8.00 g, 0.20 mol) and placed in the autoclave. The reaction was carried out for 7 h at 80 °C. The clean product 1 (33.6 g, 0.14 mol, Y = 69%) was obtained by fractional distillation as a colourless liquid (bp = 100-103 °C, d = 1.30 g/cm³). ¹H NMR (300.1 MHz, CDCl₃): δ 5.88 (ddt, ³J_trans = 17.1 Hz, ³J_cis = 10.3 Hz, ³J_H,H = 5.7 Hz, 1H, CH₂CH=CH₂), 5.30 (m, 2H, CH₂CH=CH₂), 4.14 (d, ³J_H,H = 5.7 Hz, 2H, CH₂CH=CH₂), 3.91 (t, ³J_H,F = 13.8 Hz, 2H, CF₂CH₂). ¹³C NMR (75.5 MHz, CDCl₃): δ 133.0 (CH₂CH=CH₂), 118.7 (CH₂CH=CH₂), 120.5-105.5 (C₃F₇), 73.4 (CH₂CH=CH₂), 66.3 (t, ²J_C,F = 25.8, CF₂CH₂). ¹⁹F NMR (282.3 MHz, CDCl₃): δ -81.25 (t, ³J_F,F = 9.5 Hz, CF₃), -123.60 (m, CF₂), -128.08 (s, CF₂). MS (EI), m/z (rel. ab.%): 240 (M^+°, 100%), 69 (CF₃^+°, 40%) 41 ([CH₂-CH=CH₂]^+°, 70%).

References:

Lazzari, Dario;Cassani, Maria Cristina;Solinas, Gavino;Pretto, Marisa [Journal of Fluorine Chemistry,2013,vol. 156,p. 34 - 37]