SU427919A1 - METHOD OF OBTAINING 2-METHYL-4,5-DIOXIANTHRAHIPONE DIVINEL ETHER - Google Patents

Description

one

The invention relates to a process for the preparation of divinyl ether not described in the literature on o-oxyanthraquinone, in particular 2-methyl-4,5-dioxyanthraquinone divityl ether, which, due to its high reactivity, can be used in the synthesis of lolymers, drugs, as well as intermediate products in the synthesis of other substances.

A known method for producing divinyl eff, ir ant, raquinone, is that anthraquinone is treated with sodium hydrosulfite. The resulting anthrahydroquinone is reacted with acetylene at a pressure of 20-30 atm and an ISO-200 ° C temperature.

The desired product is isolated with known methods am, and.

The application of the known vinylating reaction of the hydroxyl compounds of the anthraquinone series allows one to obtain a new ester, which possesses not only the properties characteristic of compounds of the anthraquinone series, but also new ones.

The proposed method for the preparation of 2-methyl-4,5-dioxyanthraquinone divinyl ether is that 2-methyl-4,5-dioxyanthraquinone is violated at a temperature of 20-90 ° C, preferably at 30-45 ° C and atmospheric pressure.

The desired product is isolated by known techniques. The yield of the final product up to 80. The vinylation process proceeds one-step under mild conditions, as a result of which there is no need for special equipment.

The resulting compound, a crystalline substance, dissolves in a-cetone, ethyl acetate, chloroform, does not dissolve in water and ether. Example. In a round bottom flask equipped with a reflux condenser, a dropping funnel, and a stirrer, 5.6 g (0.1 mol) KOH are placed in 100–150 ml of absolute efI | r and cooled down to 0–1 ° С and constant moving saturated with acetylene for 4 hours.

For half an hour, 50 ml of a benzene (dry) solution of 0.7 g (0.0027 mol) of 2-methyl-4,5-dioxyanthraquinoia (chrysophanoic acid) are added dropwise. The reaction mixture is saturated with acetylene to change color from dark purple to dark pink with a transition to greenish color at temperatures of 30-90 ° C for 20-30 hours. After the reaction is completed, the mixture is treated with water, the aqueous layer is extracted with ether (extraction with ether allows the unreacted starting product, chrysophanoic acid, to be completely separated) and combined with the organic layer, which is washed again

water, then-dried over calcined sodium sulphate and evaporated to dryness. The product is dissolved in benzene and passed through a layer of alumina. Additional cleaning is not required. Divinyl ether yields are 78-80%. T. pl. C. Found,%: C 73.86; H 4.22.

Cis (Hi404.

Calculated,%: C 74.50; H 4.57. IR spectrum (, КВг) 1610-11676 cm- (С О), 1640 cm (), 1080-1090 cm (, С-О-R-), there are no bands of OH-groups.

A quantitative reservation was made to prove the structure of the resulting divinyl ether. Received tetrabromide with so pl. 285-287 °.

Found,%: C 36.81; H 2.94; Br 50.90.

 Ci9Hi4-04Br4.

Calculated,%: C, 36.42; H 2.24; Br 51.12.

Next, the divinyl ether is hydrogenated on

Pd-mobile at room temperature, at

this absorbs the calculated amount

hydrogen. DIETHYLIDE ester of chrysophanol is isolated with m.p. 174-176 ° C. - IR spectrum (KVg)

1630, 1665 cm- (C O), 1080-1090 cm

(С-О-R-), bands - oscillations of OH-groups and

there are no double ethylene bands.

Subject invention

Claims (2)

1. A method for producing divinyl ether. 2-methyl-4,5-dioxyanthra and "it, characterized in that 2-methyl-4,5-dioxyanthraquinone subjected to vinylation at 20-90 ° and atmospheric pressure, followed by separation of the target product by known methods. 2. A method according to claim 1, characterized in that the process of vinyl is carried out at 30-45 ° C.