2- succinic anhydrid

FIGURE 6.10 1 = Camphene, 2 = Succinic anhydride, 3 = Camphor, 4 = Bomeol, 5 = Furancarboxaldehyde (Furfural), 6 = Hydroxymethyl furancarboxaldehyde, 7 = Levoglucosan. 

Polymers other than polynucleotides also have been found to induce interferon. Pyran-2-succinic anhydride, 4,5-dicar-boxy tetrahydro- 6-methyl- anhydride polymers in low daily doses protect mice infected with lethal doses of Friend or Rauscher leukemia virus. A correlation between degree of protection and interferon levels was noted. Vinyl sulfate polymers and divinyl ether-maleic acid copolymers induce interferon and protect mice against lethal virus infections. Both of these substances had activity that could not be accounted for by interferon alone. The dependency on molecular weight of polyacrylic acid polymers for interferon induction indicated a... 

H02C(CH2)2C02H. Colourless prisms m.p. 182 C, b.p. 235°C. Occurs in amber, algae, lichens, sugar cane, beets and other plants, and is formed during the fermentation of sugar, tartrates, malates and other substances by a variety of yeasts, moulds and bacteria. Manufactured by the catalytic reduction of maleic acid or by heating 1,2-dicyanoethane with acids or alkalis. Forms an anhydride when heated at 235°C. Forms both acid and neutral salts and esters. Used in the manufacture of succinic anhydride and of polyesters with polyols. 

The polyispbptylenes (PIB) having molecular weights ranging from 1000 to 2000 are substituted by maleic anhydride, and the polyisobutylene succinic anhydride (PIBSA) formed is neutralized by a polyethylene-polyamine as indicated in Figure 9.10. 

Benzoic acid Succinic. anhydride Hexacetyl mannitol ... 

In the following preparation, this reaction is exemplified by the union of anthracene with maleic anhydride, to form 9,io-dihydroanthracene-9,io-e do-a -succinic anhydride note that as a result of this reaction both the outer rings of the anthracene system become truly aromatic in character. 

B) Acetic, succinic anhydride phthalic anhydride (and substituted derivatives). 

To distinguish these anhydrides from the corresponding acids, note that succinic anhydride (m.p. 120°) is almost insoluble in cold water, whereas succinic acid (m.p. 185 ) is readily soluble. Phthalic anhydride has m.p. 132° and phthalic acid has m.p. 196-199° with decomposition. Each of these anhydrides when heated with water hydrolyses to the corresponding acids. 

The fluorescein test for succinic acid (p. 349) and the phthalein and fluorescein tests for phthalic acid (p. 351) are obviously given also by succinic anhydride and phthalic anhydride, as these tests depend upon the initial formation of the anhy dride in each case. 

Method A. In a 500 ml. round-bottomed flask, fitted with a reflux condenser attached to a gas trap (Fig. II, 13, 8), place 59 g. of succinic acid and 117-5 g. (107-5 ml.) of redistilled acetyl chloride. Reflux the mixture gently upon a water bath until all the acid dissolves (1-2 hours). Allow the solution to cool undisturbed and finally cool in ice. Collect the succinic anhydride, which separates in beautiful crystals, on a Buchner or sintered glass funnel, wash it with two 40 ml. portions of anhydrous ether, and dry in a vacuum desiccator. The yield of succinic anhydride, m.p. 118-119°, is 47 g. 

Method B. In a 500 ml. round-bottomed flask, provided with a reflux condenser protected by a cotton wool (or calcium chloride) drying tube, place 59 g. of succinic acid and 102 g. (94-5 ml.) of redistilled acetic anhydride. Reflux the mixture gently on a water bath with occasional shaking until a clear solution is obtamed ca. 1 hour), and then for a further hour to ensure the completeness of the reaction. Remove the complete assembly from the water bath, allow it to cool (observe the formation of crystals), and finally cool in ice. Collect the succinic anhydride as in Method A. The yield is 45 g., m.p. 119-120°. 

Perform the followmg experiment with succinic anhydride. This illustrates the formation of an anilic acid, which is usually an excellent... 

A further example is given below illustrating the use of a dibasic anhydride (succinic anhydride) the succinoylation reaction is a valuable one since it leads to aroyl carboxylic acids and ultimately to polynuclear hydrocarbons. This general scheme of synthesis of substituted hydrocarbons through the use of succinic anhydride is sometimes called the Haworth reaction. Thus a-tetralone (see below) may be reduced by the Clemmensen method to tetralin (tetrahydronaphthalene) and the latter converted into naphthalene either catal3d.ically or by means of sulphur or selenium (compare Section, VI,33). 

The preparation of the cyclic ketone a-tetralone possesses a number of interesting features. Succinic anhydride is condensed with pure benzene in the presence of anhydrous aluminium chloride (slightly over two equivalents see 1 above) to yield (3-benzoylpropionlc acid ... 

Anthracene and maleic anhydride. In a 50 ml. round-bottomed flask fitted with a reflux condenser, place 2 0 g. of pure anthracene, I 1 g. of maleic anhydride (Section 111,93) and 25 ml. of dry xylene. Boil the mixture under reflux for 20 minutes with frequent shaking during the first 10 minutes. Allow to cool somewhat, add 0 5 g. of decolourising carbon and boil for a further 5 minutes. Filter the hot solution through a small, preheated Buchner funnel. Collect the solid which separates upon coohng by suction filtration, and dry it in a vacuum desiccator containing paraffin wax shavings (to absorb traces of xylene). The yield of adduct (colourless crystals), m.p. 262-263° (decomp.), is 2-2 g. Place the product (9 10-dihydroanthracene-9 10-cndo-ap-succinic anhydride) in a weU-stoppered tube, since exposure to air tends to cause hydration of the anhydride portion of the molecule. 

Supplement (combined with Volumes XVIII and XIX) XVII, 2nd 1934 2359-3031 Hydroxy compounds Furfuryl alcohol, 112. Carbonyl compounds Butyrolactone, 234. Furfural, 272. 2-Aoetyl-thio-phene, 287. Xanfhone, 366. Succinic anhydride, 404. Phthalio anhydride, 469. 

It will be easy to put in bond a because it is para to the MeO group, but bond b might be difficult Tire strategy is to put in bond a first and use an intramolecular reaction to force bond b to go in the right place. Succinic anhydride is a convenient four carbon electrophile ... 

Succinic anhydride the structure of which is shown is a cyclic... 

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