Water → 3-Methoxy-1,1,1,5,5,5-hexafluoropent-2-ene

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Reaction Steps

21.1 g (0.12 mol) of bis(trifluoromethyl)allene were added to 20 mL 0.5 N NaOCH3 in methanol (8 mol % relative to allene) over 1 h with water bath cooling, keeping the reaction temperature at 10-20° C. Stirring was continued for 15 min. and the mixture poured into 80 mL cold water. The lower layer was separated and the aqueous portion extracted with 20 mL CH2Cl2. The combined organic layers were washed with 5 mL brine, dried (Na2SO4) and distilled to give 21.9 g (88% yield) of CF3CH=C(OCH3)CH2CF3, boiling point 110-111° C. IR: 1672 cm-1. Major MS fragments: 208 (75.9), 189 (30.2), 158 (31.6), 125 (60.5), 111 (82.4), 91 (100), 31 (91.2). 1H NMR:4.95 (q,1H, J=7.5 Hz), 3.65 (s, 3H), 3.18 (q, 2H, J=9.8 Hz) ppm. 19FNMR: -54.4(d,3 F), -63.9 (t, 3 F) ppm. Anal. Calcd for C6H6F6O: C, 34.61; H, 2.91. Found: C, 34.59; H. 2.85.

Provenance & Evidence