[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C-:17]#[N:18].[K+]>O1CCCC1.O.O1CCOCCOCCOCCOCCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:17]#[N:18])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1A stirred mixture of 5.0 grams (0.021 mole) of 4-fluoro-3-phenoxyphenylmethyl chloride, 4.1 grams (0.063 mole) of potassium cyanide and 0.6 gram (0.002 mole) of 1,4,7,10,13,16-hexaoxacyclooctadecane in 180 ml of tetrahydrofuran was heated at reflux for about four hours. After this time the reaction mixture was diluted with 180 ml of water, and then extracted with two 100 ml portions of diethyl ether. The combined ether extracts were washed with five 200 ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 5.4 grams of 4-fluoro-3-phenoxyphenylacetonitrile. The nmr spectrum was consistent with the proposed structure.
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