SU395356A1 - METHOD OF OBTAINING CHLORIDIENE KETONES - Google Patents

Description

one

A method is proposed for the preparation of chlorine-containing diene ketones, which are of great interest for the synthesis of rubber-like polymers, copolymers, as well as bleaching and fragrances.

When using the Friedel-Crafts reaction in organic chemistry, a number of compounds not described in the literature were obtained.

The proposed method for the preparation of Chlordienic iKeTOHOiB is that the e-nin and chlorine-containing diene interact with acetic acid chloride in a solvent at minus 5 - plus 10 ° C in the presence of Friedel Crafts catalysts, followed by separation of the target product by known methods.

Due to the presence of carbonyl and diene groups, the resulting chlordiene ketones have a higher reaction rate, which makes it possible to use them as monomers.

The proposed method is simple to implement and allows to obtain the target products with a yield of 48-bb / o.

Example 1. In a round-bottomed flask, watered with a mechanical stirrer, refluxed with refrigerant | M, heat meter and an air funnel, 39.5 e (0.5 mol) of acetyl chloride dissolved in 50 ml of carbon tetrachloride are placed. When cooled, 67 g (0.5 mol) of aluminum chloride is introduced into the mixture so that the temperature of the mixture does not increase above minus 5 ° C. Then, at minus 10 minus 15 ° C, 61.5 g (0 , 5 mol) 2,3-dn-chlorobutadiene-1,3.

After that, the contents of the flask are treated with a mixture of hydrochloric acid, ether and ice. a-Acetyl-2,3-di1-HLOrbutadiene-1,3 is extracted with ether, washed with water, 1Oi / o-HbiM soda, dried with calcium chloride and the residue is distilled off in vacuo. 54 g (67.9 / o), a-acetyl2, 3-dichlorobutadiene-1,3, t. Bales were isolated. 97 ° C / 5 mmHg v .; 1.5250; df 1.2741; found 39, 69, calculated 38.72.

Found / /: C1 43.48.

Sbnbsio

Calculated, C1 43.29. Example 2. In a flask placed 22 g (0.3 mol) of acetyl chloride. Upon cooling, 21 g (0.15 mol) of aluminum chloride is added so that the temperature of the mixture does not rise above minus 5 ° C. Then 20 g of 2,3-di is introduced at minus 10 - minus 15 ° C for 1 hour. chlorobutadiene-1,3, after which the contents of the flask are treated as indicated in example 1.

Example 3. In a round-bottomed flask load 16 g (0.2 mol) of acetyl chloride,

boiled in 20 ml of methylene chloride. When cooling the IK mixture (28 g (0.2 mol) of chlorine aluminum is added) so that the temperature of the mixture rises above minus 5 ° C. Then, at minus 10 - minus 20 ° C, vinyl acetylene is passed through for 3 hours After which the contents of the flask are treated with a mixture of hydrochloric acid, ether and ice, the a-Acetylchloroaprene is extracted with ether, washed with water, 10 O / O is dissolved with calcium and dried with calcine after distillation of the ether. 13.3 g of () α-acetylchloroprene, m.KIP 53 ° C / 2 mmHg / g |, about 1.5075; rff 1.2662; MRc; found 34.49, calculated 33, 86

Found, o / o: C 55.67; H 6D2, C1 26.92.

SbN7S1O

Calculated, "/ o: C 55,17; H 5.36; .C1 27.20.

P (p and measures 4. Analapi1CH1N01Iz6,6g (0.1 mol)

nsopropenylacetylene, 14 g (0.1 mol) of aluminum chloride and 8 g (0.1 mol) of acetic chloride, 7 g (48.27%) of a-acetylchlorisoprene, m.p. 86 ° C / 5 mmHg v .; nj 1,4990; df 1,1179; MRo. Found 38.80, calculated 38.46.

Found, “/ o: C1 25.20.

Sundou

Calculated, o / o: C1 24.63.

Subject: W oh and e and

The method of producing hlardian ketones, characterized in that yenin and chlorine-containing, is subjected to interaction with acetyl chloride in a solvent at minus 5 - plus 10 ° C in the presence of Friedl-Crafts catalysts with subsequent, and 1M isolation of the target product by known methods.