SU395355A1 - The method of producing alkoxy or dialkoxy - Google Patents

Description

one

The invention relates to a method for producing substituted benzenes, in particular alkoxy or dialkoxy (2-cyclohexen-1-yl) benzenes, which can be used as physiologically active substances, high molecular weight monomers and intermediates in organic synthesis.

A known method for producing alkoxy- (2cy1-clohexen-1-yl) -benzenes is obtained by reacting the corresponding magnesium-: or organolithium compound with 3-bromo-cyclohexene in an organic solvent, for example tetragvdrofuran. The target product is isolated by known methods; its yield does not exceed 40%.

In order to increase the yield and enhancement of the assortment of target products, a method for producing alkoxy dialkoxy (2-cyclohexbn-1-yl) benzenes is proposed, which means that alkoxy or dialkoxybenzenes are reacted with 1,3-cyclohexadiene in the presence of ortho-phosphoric acid as a catalyst in carbon tetrachloride. The target product is isolated by known methods, its yield is 60-90%. The process is preferably carried out at a ratio of alco-or dialkoxybenzene, 1,3-cyclohexadiene and catalyst 2: 1: 0.5 - 4: 1: 075.

The proposed method allows, in addition to known compounds, to produce dialkoxn- (2-cyclohexen1-yl) benzenes not specified in the laboratory.

Example 1. Preparation of methoxy- (2-cyclohexen-1-yl) benzene,

To a mixture of 43.26 g (0.4. Mol) anisole, 7.35 g (0.075 mol of orthophosphoric acid and 15.4 g (0.1 mol) of carbon tetrachloride, cooled to 4-6 ° С, for 1 hour with vigorous stirring, a solution of 8 g (0.1 mol} of 1.3-sylcclog.xadiea in 15.4 g (0.1 mol of carbon tetrachloride) is added. The reaction mixture is then heated to 40-45 ° C, stirred for 6 hour and treated as indicated in the general procedure: 14.6 g of methoxy- (2-cyclohexen1-yl) benzene are obtained, yield 78%.

The product is a colorless liquid with m.p. 105-106 ° C / 3 .i. “Pg. v .;

MRo- found 57.98, “20d 1.5486; d, 1.0322; calculated 57.60.

Paideno,%: C 82.89; H 8.53. C.sHieO 82.93; H 8.56. Calculated. %: WITH

Example 2. Obtaining 1,3-dimethoxy- (2cyclohexane-yl) benzene.

To a mixture of 55.2 g (0.44 mol} of 1,3-dimethoxybenzene. 4.9 g (0.05 mol} of orthophosphoric acid and 15.4 g (0.1 mol) of carbon tetrachloride, cooled to 4-6 ° C, for 1 hour while being intensively moved, and a solution of 8 g (0.1 mol) of 1,3-cycloxadiene in 15.4 g (0.1 milliliters) of tetrachloride ultralite are added to the solution. Then the reaction mixture is heated to 20-25 ° C and stirred for 4 hours, after which it is treated as indicated in your method, 19.0 g of 1,3-dimethoxy- (2-cyclo-w-xen-1-yl) benzene are obtained, yield 90%. The product is a colorless liquid with m.p. 119-12G C / 3 mmHg; nj ° 1.5 516; df 1.0780; MRo. Found 64.64, calculated 63.86.

Found,%: C 76.94; H 8.68.

CuHisOa Calc., C, 77.07; H 8.31.

Example 3. Preparation of 1,2-dimethox (2-cyclotech sen-1-yl) benzene.

To a mixture of 27.6 g (0.2 ml) of veratrol, 4.9 g (0.05 mol) of orthophosphoric acid and 15.4 g (0.1 mol) of tetrachloride carbon, cooled to 4-6 ° С, during Under intensive stirring, 1 hour is added. A solution of 8 g (0.1 lit) of 1,3-cycloexadiene in 15.4 g (0.1 mol) of carbon tetrachloride. The reaction mixture is taken up to 40-45 ° C and kept under stirring for 6 hours, then treated as indicated in the general procedure, and 13.0 g of 1-2-dimethoxy- (2c; cyclohexyl-1-yl) are obtained. , yield 60%. The product is a colorless liquid with m.p. 142-143 ° C / 3 mmHg v .; 1.5532; df 1.0785; ,; found 64.79, calculated 63.86,

Found%:

C C

8.34.

77.24;

H C 4Hi6O2 Calculated,%:

H 8.31. 77.07;

Subject invention

Claims (2)

1. A method for producing alkoxy- or dialkoxy- (2-cyclohexen-1-yl) benzenes, characterized in that, in order to increase the yield and expand the assortment of target products, al: coxy or dialkoxybenzene is reacted with 1,3- cyclohexadiene in the presence of a catalyst - orthophosphoric acid - in an environment of carbon tetrachloride with the release of the target product by known methods. 2. A process according to claim 1, characterized in that the process is carried out with a ratio of alkoxy or dialkoxybenzene a, 1,3-diclohexadiene and catalyst, respectively, equal to 2: 1: 0.5-4: 1: 0.75.