DE233327C - - Google Patents

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- JVl 233327 CLASS 12 #. GROUP.

Patented in the German Empire on March 30, 1910 .

It has been found that phenyl esters of iodine-substituted fatty acids can be obtained, if iodized fatty acids or their derivatives are esterified with phenols in the usual way, introduces iodine into phenyl esters of unsaturated fatty acids or the phenyl esters of chlorine or bromine-substituted fatty acids treated with alkaline iodine or alkaline iodine.

Possess the new esters so presented

ίο valuable therapeutic properties and should be used as a remedy. They combine the effects of iodine and that of the phenols used.

j, example i.

100 parts of phosgene in benzene solution are allowed to run into a solution of 186 parts of iodoacetic acid, 200 parts of pyridine and 94 parts of phenol in 500 parts of benzene, with cooling and stirring. When the reaction has ended, it is washed with hydrochloric acid and then with dilute sodium hydroxide solution, and the benzene solution dried on it is cooled after the benzene has evaporated. The residue that remains solidifies and is recrystallized from alcohol. The phenyl iodoacetate thus obtained forms needles with a silk sheen from FP 75 to 77 °, which are difficult to dissolve in water and more easily soluble in alcohol and benzene.

Example 2.

150 parts of thymol are in 130 parts of di-

Dissolved methylaniline and 500 parts of benzene, a solution of 205 parts of iodoacetyl chloride was added. When the reaction is complete, the procedure is as in Example 1 and the iodoacetylthymol formed is distilled in vacuo. It forms an oily liquid at room temperature from the SP 176 to 178 ⁰ (mm under 10) of schwachgelbei ⁷ color, is odorless and tasteless and readily soluble in common organic solvents.

Example 3.

200 parts of a-bromoisovalerianyl chloride or the corresponding amount of bromide are dissolved in the same amount of benzene and added to Given 124 parts of guaiacol and 100 parts of pyridine. After the reaction has ended, the C.-Bromoisovalerianylguaia-cholesterol iso-formed. From alcohol crystallizes it forms coarse, colorless, odorless and tasteless Crystals from the F. P .; 69 to 70 °.

287 parts of this ester are mixed with 300 parts of alcohol or another suitable solvent poured over and after adding about 175 parts of sodium iodine or the equivalent Potassium iodine or calcium iodine is heated for a long time until the reaction is complete. At the When cooling down, the new ester crystallizes out almost completely. One sucks off the crystal pulp, washes salt-free with water and recrystallizes from a little alcohol. The α-iodoisovalerianyl guaiacol Melts at 76 to 79 °, forms rather coarse, colorless and odorless and tasteless Crystals that are difficult to dissolve in water, more easily soluble in warm alcohol, benzene and chloroform. If you melt a little Amount with soda, acidify the melt dissolved in water with dilute sulfuric acid

and if a little sodium nitrite is added, iodine precipitates in crystalline form, which is in chloroform dissolves with purple paint.

The α - Jodisovalerianylkreosotester forms a thick oily liquid that with prolonged Standing solid crystals separate.

The guaiacol ester of methylpropyliodopropionic acid

CH

³ \

C _a H _r

CH-CHJ-COOC ₆ H ^ Ch ₃

forms like methylpropylbromopropionic acid guajakol ester, from which it is obtained in the same way as described in Example 3, at ordinary temperature a pale yellow, oily, tasteless and odorless liquid.

The α-iodine -n-butyric acid guayakol ester is liquid and boiling at 185 ° (10 mm), the α-bromo-η -butyrylguajakol used for its representation boils at 165 ° under the same pressure and is liquid.

Example 4.

80 parts Guaj akol are mixed with 300 parts and 40 parts Jodbehensäure Phospliortrichlorid and as long heated at 110 to 120 ^0, until the development of hydrochloric acid terminated. The reaction product is then washed until the washing water reacts neutral and the ester which has separated out is dried, preferably in an ethereal solution. The ester forms a thick, honey-yellow oil that is soluble in common solvents.

Example 5.

Made from 110 parts of hydroquinone and 500 parts α-Bromisovalerianyl bromide is obtained according to Example 2 the di-a-bromoisovaleric acid ester of hydroquinone of the constitution

C _d

shown, the colorless and tasteless melting at 53 °, in alcohol and ether forms easily soluble needles.

220 parts of this ester are dissolved in 250 parts of alcohol and 180 parts of sodium iodine warmed up on the water bath for a long time. The alcohol is distilled off and the Residue in water and crystallizes the oily precipitated, soon solidifying di-α-iodisovalerianylhydroquinone from little alcohol. It is obtained in the form of almost colorless, odorless and tasteless needles from the F.P. 85 to 87 °, which are easily soluble in ether and benzene and sparingly soluble in water.

Example 6.

125 parts of oleic acid guayakol ester are used in 150 parts of glacial acetic acid, which is 10 percent hydrogen chloride contains and is mixed with 65 parts of sodium iodine, registered and several Heated to 50 to 60 ° for hours. The oil is then poured into water, removing any that has formed free iodine with sulphurous acid, then separates the ester and dries it. Of the Iodostearic acid guayakol ester forms a yellow-red oil with a mild oil smell and taste, which dissolves in common organic solvents.

The procedure is analogous to the representation of other of the named bodies, like the α-iodoisobutyric acid guajakol ester (S.P. 160 to 175 ° at 15 mm pressure). .

Claims (1)

Patent claim: Process for the preparation of phenyl esters of iodized fatty acids, consisting therein that iodized fatty acids or their derivatives are esterified with phenols into phenyl esters of unsaturated fatty acids introduces iodine or the phenyl esters of chlorine or bromine-substituted fatty acids with alkaline iodine or alkaline iodine.