DE165897C - - Google Patents

Description

'nezCi cficw- 3ca & n famtih .

PATENT OFFICE.

165897 CLASS 12 o.

It has been found that the benzylic isovalerate the formula:

CH ₉ 'CO 0'CH ₉ - C _R H

possesses valuable therapeutic properties. This new ester is made from the stomach very well tolerated and excellently absorbed. Before the well-known isovaleric acid derivatives

ίο he is particularly characterized by his pleasant, aromatic odor and its complete harmlessness to the gastric mucosa the end. As a result of these good properties, the new ester has proven to be a valuable one Sedative proven.

In Mindes Manuals of New Medicines, p. 244, there is a body called Validol described, which is referred to as an elerate of valerate. · This body but is actually not a chemical individual, but a mixture of different bodies with valeric acid elemetate. This mixture also lacks the sedative present in benzyl isovalerate acting benzyl group. From the one mentioned in the Bulletin de la Societe Chimique 1896 on p. 297 "Valerate de benzyle" of the formula:

^C *

COO-CH ₉ -C ₆ H ₅

the new product already differs chemically in that it is a derivative of the ß-Dimethylpropionic acid and not, like the ester mentioned first, that of methylethylacetic acid is. The preparation described in the bulletin is an optically active body, made from active valeric acid, of which a physiological effect as opposed to that of the starting material of the new ester-forming isovaleric acid, the so-called valeric acid, is not known. To prepare the new compound one proceeds in such a way that one benzyl alcohol or its derivatives with isovaleric acid or their derivatives by one of the methods customary for the preparation of esters esterified.

Example 1.

25 parts of benzyl chloride and 25.2 parts of sodium isovaleric acid are heated to 160 ° in an oil bath on a reflux condenser for 10 hours. The cooled mass is then mixed with benzene and water and shaken well. The aqueous salt solution is separated from the benzene solution of the ester, the latter is freed from adhering acid by shaking with dilute soda solution and dried over calcium chloride. After filtration, the benzene is distilled off and the remaining oil is subjected to fractional distillation in vacuo. ¹ V

The benzyl isovalerate boils at 136 ^° under 25 mm pressure. It is a colorless, pleasantly smelling oil.

In the example above, the benzyl chloride can be used with the same success by the equivalent amount of benzyl bromide or benzyl iodide to be replaced.

Instead of sodium isovaleric acid

The potassium salt or other salts of isovaleric acid can also be used will.

g Example 2.

To a solution of 10.8 parts of benzyl alcohol and 7.9 parts of pure pyridine in 20 parts of dry benzene are allowed to slowly and with stirring a solution of

ίο 12.05 parts of isovaleryl chloride in 20 parts run in dry benzene. The reaction to benzyl isovalerate begins when heated and hydrochloric acid pyridine, which separates out of the solution as a white crystal mass. The reaction mass is then heated about an hour on the water bath at the reflux condenser, let cool and add ice water and excess diluted Hydrochloric acid added. When this mixture is shaken, the hydrochloric acid pyridine goes off in solution. The benzene solution of the new ester is separated from the aqueous layer, extracted again with very dilute hydrochloric acid, isolated over calcium chloride dried and from the resulting solution of benzyl isovalerate, such as described in Example 1, obtained.

Example 3.

A mixture of 11 parts isovaleric acid and 10 parts of benzyl alcohol is carefully mixed with 1.1 parts of concentrated sulfuric acid added and the mixture thus obtained is heated on the water bath for 12 hours. After the reaction has ended, the reaction mass is poured into ice water, shaken out with ether, the ethereal solution lifted off, shaken with dilute soda solution and the isovaleric acid benzyl ester distilled after removal of the ether in vacuo.

The esterification can also be carried out by introducing dry hydrochloric acid gas into a heated one Mixture of isovaleric acid and ■ benzyl alcohol. ■

Example 4.

108 parts of benzyl alcohol and 129 parts of quinoline are dissolved in four times the amount of dry benzene and 99 parts of phosgene are introduced into the solution thus obtained, with cooling and stirring. To dissolve the hydrochloric acid quinoline separated out during the reaction, water is then added, the benzene solution separated from the aqueous layer is washed with water, dried over calcium chloride and the benzene is distilled off in vacuo. The remaining benzyl chloroformate of the formula Cl ■ CO O — _{CH 2 —C 6} i / _{5 is then} heated for about 6 hours with an equivalent amount of sodium isovalerate to about 160 ° and the benzyl isovalerate is isolated from the reaction product as indicated in Example 1.

Example 5.

19 parts of isovaleric anhydride are added along with 11 parts of benzyl alcohol Heated for 6 hours to 180 to 200 °. The reaction mass obtained in this way becomes on the benzyl isovalerate isolated by fractional distillation in vacuo.

Claims (1)

Patent claim: Process for the preparation of benzyl isovalerate, consisting therein that one benzyl alcohol or its suitable for the preparation of benzyl esters Allow derivatives to act on isovaleric acid or its derivatives.