SU688492A1 - Method of preparing 3,4-dimethoxy- or 3,4-methylenedioxyphenols - Google Patents

Description

This invention relates to the acquisition method of 3,4-D 1-toxin 3,4-methylenic SIPHENOLS, which are: HC ONE.

Compound, ne, or m1H for the synthesis of veins: avenues, possessing potentials of anaden: lnoy activity, and, moreover. 3.4-methylenoxynol is the starting material for the synthesis of compounds, possessing their juvenile activity.

The known method of lolce ing 3,4-dimethoxy- or 3.4-methyldioxyphenols by oxidation with 3.4-dimetho-or 3,4-methylenedioxnbenzaldegnda with 20% naduc-acetic acid at a temperature of 32 ° C in acetic acid with subsequent purification n; derivative

The yield of the target product 49-50%.

The shortage of a well-known method is the relatively low yield of the target product.

The purpose of the invention is to increase the yield of the target product.

This goal is achieved by the method of obtaining 3,4-d1methoxy- or 3,4-methylenedioifbnol oxides of the corresponding substituted benzaldepids with adcarboxylic acid in an organic solvent and saponification of the resulting formyl derivative followed by isolation of the target product, which has a distinctive feature: at

nadcarbo.nova acid is used as a supramide. sin; nuyu, as lacTBopntel - chloroform and riiponccc are conducted at a temperature from -4 to 0 ° C.

The proposed method is to prevent the target product with a yield of 75-85%.

Process NRP peremenivanpi within 2--2.5 /. the image of the formula derivative is washed without purification.

Iadmuraginhyu acid is ready1 t from 26 - 28% perhydrol and formic acid with a concentration of 85-99% is unpredictable before the reaction.

PROGRAM 1. 11p, iiacTBOpa formic acid preparation.

A mixture of 250 ml of 99% formic acid and 60% of 26-28% perhydrol was heated to 60 ° C. Then cooled to 0 ° C. To a solution cooled to -4 ° C, 33.2 g (0.2 mol) 3.4 -.A11methoxybenzaldehyde in 150 ml of x.oroform with stirring 1H1 .I1I and external cooling is added dropwise the prepared solution of n-formic acid so that the temperature of the reaction ion does not exceed 0 ° C.

The control of the process is carried out with the help of those in chloroform, the sediment from the reaction mixture onto Silufol plates and 1 in UV-UV light. The solution of the solution of the subframe acid and irradiation from, O1da will show the chromatogram: check the initial aldehyde (after 2 2, 5 h). After the addition is complete, the mass is stirred for 30 minutes. Then: ENT;) layer is separated, lro. Washed with water, NajSOg solution, water. Chlorofolp was distilled off, a 10% amount of 10% is added to the residue, B) Huviochi D110 and 1 g of NagSOs and boiled until full (20-30 minutes).

The solution is cooled, iodic acid is added with hydrochloric acid, and extracted with benzene. Thipa T is washed with water, dried with Na2SO4, filtered through a layer of silicon. The clarified extract of u-nar.

25.5 g (83%) of 3,4-dimethoxyfeiol are obtained.

Ave. 2. OXYLESHELE 3,4-metlep.n.1loxnbenzaldeg1) 1da and the next sapranium} 1 of gfo formate, water is similar to P; rmsei I.

3,4-methyl 11dpoxyfepol is obtained with a yield of 85%.

Ex. 3. A solution of subframeic acid is prepared from 250 ml of 92% formic acid 11 60 ml of 26-28% iergndrol, similar to irishmere 1.

OchSlenna 3,4-methyl; 1D1YUK, SNBEN; aldehyde and the subsequent saponification of 1 | 5ormiata of life period t and | NaL | OG11chnachno example 2.

3.4-methylene dioxy 11 feiol is obtained with a yield of 79%.

PRI me R 4. The solution of formic acid is prepared from 250 l / l, 85% formic ivHLVioTbi and 60 .. 26-28% Ner1M1Drol analornno nrlmer. O.Cleslnna 3,4-met11landnoxybenzaldepn.1a and the next formate were applied as described in Example 2.

Get 3,4-Methlenda. 1.conf, nol - with a yield of 75%.

F o r M o l a and 3 obr e ;; H

The method of obtaining 3,4-dimethoic- or 3,4.VI ethn of the windows of the phenols by oxidation of the corresponding reputable benzaldehydes with supracarboxylic acid in an organic solvent and saponification of the resulting formyl derivative with the Next} -1-dimer, the lower of the target product, I had a different setting, I did not have a different setting, I did not have a different setting, I didn’t have a different sample product, and I didn’t have a different target product, I did not have a different setting, I didn’t have a different setting, I didn’t have a different product, I didn’t have a different target product, I didn’t have a different sample product, and I had a different situation, I didn’t have a different target product, I didn’t have a different sample product, and I had a different setting, I didn’t have a different target product, I didn’t have a different sample product, I didn’t have a different sample product, and I had a different sample product. that, in order to increase the yield of the target product, nadkarbo izi () th 1 acid is used as tartaric acid, as a boron1 body is chlorofoem and the process is carried out from 4 to 0 ° C.

iifor, .ma1tsgp,

RULES 30 expertise

i. Orphanos D. G. and Taiirins A. Preparation of 3,4-methylendioxy- and 3,4-dimetoxy G-aminofenol, Canad, - J “of Chemistry. 44 9G6, p. 1875-1877 (irototpi).