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Fumaryl chloride

Acid Chloride Formation. Monoacid chlorides of maleic and fumaric acid are not known. Treatment of maleic anhydride or maleic acid with various reagents such as phosgene [75-44-5] (qv), phthaloyl chloride [88-95-9] phosphoms pentachloride [10026-13-8] or thionyl chloride [7719-09-7] gives 5,5-dichloro-2(5JT)furanone [133565-92-1] (4) (26). Similar conditions convert fumaric acid to fumaryl chloride [627-63-4] (5) (26,27). NoncycHc maleyl chloride [22542-53-6] (6) forms in 11% yield at 220°C in the reaction of one mole of maleic anhydride with six moles of carbon tetrachloride [56-23-5] over an activated carbon [7440-44-4] catalyst (28). [Pg.449]

Under Friedel-Crafts conditions, /n j -l,2-dibenzoylethylene [959-28-4] is synthesized by the reaction of one mole of fumaryl chloride with two moles of benzene (30) (see Friedel-CRAFTSreactions). [Pg.449]

Fries rearrangement, 21, 25 Froth dissipation, 20, 3 Fumaryl chloride, 20, 29, SI 2-Furanacrylic acid, 20, 55 F uran, 2-(bromomethyl)tetrahydro-, 23, 88... [Pg.58]

The reaction mixture is heated by means of an oil bath (inside temperature 130-135°) for two hours, taking care to avoid overheating (Note 5), and then allowed to cool to 90-95°. The fumaryl chloride is distilled as rapidly as possible (twenty minutes), and the portion boiling over a 250 range (6o-85°/i3 i4 mm.) is collected. It is then redistilled slowly (one hour), and the portion boiling over a 2° range (62-64°/i3 mm.) is collected (Note 6). The yield is 125-143 g. (82-95 Per cent °f the theoretical amount) (Notes 7. and 8). [Pg.27]

Fumaryl chloride is best preserved in sealed glass containers. Bottles, closed by rubber stoppers free from sulfur, can be used for short periods. Ground glass-stoppered bottles are unsuitable, the joints readily becoming frozen, owing to hydrolysis of the chloride. [Pg.28]

Fumaryl chloride has been prepared from fumaric acid and phthaloyl chloride,3 from maleic acid by the action of thionyl chloride in the presence of zinc chloride, and from maleic anhydride by the use of phthaloyl chloride in the presence of zinc chloride.4... [Pg.28]

Eighteen hundred cubic centimeters of benzene (Note 1) and 350 g. of finely ground, anhydrous aluminum chloride (2.6 moles) (Note 2) are placed in a 3-I. three-necked flask, fitted with a mechanical stirrer, a dropping funnel (Note 3) containing 153 g. (1 mole) of fumaryl chloride (p. 51), and a reflux condenser (Note 4). A trap for absorbing hydrogen chloride (Org. Syn. 14, 2) is attached to the condenser. [Pg.74]

The mixture is well stirred and heated externally by hot water (50-60°) (Note 5), the water removed, and the fumaryl chloride admitted at a brisk rate, moderated only enough to avoid a too rapid evolution of hydrogen chloride this requires fifteen to twenty-five minutes (Notes 6 and 7). The mixture turns dark red and soon reaches the boiling point hydrogen chloride is rapidly given off. The mixture is then refluxed gently for ten minutes with stirring. [Pg.74]

A dropping funnel is preferred to the ordinary separatory funnel, since the rate of addition of the fumaryl chloride is important. [Pg.75]

If the mixture is not heated before the fumaryl chloride is added the reaction is slow, and when the temperature finally rises the accumulated chloride and intermediates react so vigorously that frothing and boiling over occur. [Pg.75]

If for any reason stirring is interrupted, the addition of fumaryl chloride must be stopped immediately, and the stirrer started again very cautiously. [Pg.75]

With maleimide the endo adduct (93) results at 25 °C, but the exo adduct (94) at 90 °C the endo adduct also yields the exo adduct on heating. Reaction of furan with maleic acid in water occurs slowly and the adducts readily revert thermally to the addends. As expected, the rate of formation of the endo adduct (95) is initially faster than that of the exo adduct (96), but after 10 days the ratio is 1 1 both isomers may be isolated (73T2491). Fumaric acid only adds in poor yield to furan under ordinary conditions, but this may be overcome by use of fumaryl chloride (79CC542). [Pg.620]

IJ Trienes.1 These trienes can be prepared in moderate yield by Pd-cat-alyzed reaction of fumaryl chloride (1) with 1-alkenes in the presence of N-ethyl-morpholine (2), which is superior to Bu3N as the base. (E,E)-5-Phenyl-2,4-pentadienyl chloride (3) can also be used in the condensation (last example), but this reaction is not (E,E,E)-specific. [Pg.246]


See other pages where Fumaryl chloride is mentioned: [Pg.426]    [Pg.635]    [Pg.113]    [Pg.39]    [Pg.73]    [Pg.472]    [Pg.46]    [Pg.56]    [Pg.17]    [Pg.85]    [Pg.85]    [Pg.86]    [Pg.32]    [Pg.51]    [Pg.51]    [Pg.53]    [Pg.115]    [Pg.426]    [Pg.635]    [Pg.401]   
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