SU539533A3 - The method of obtaining salts of 4-oxo-4n-1benzopyran-2-carboxylic acid - Google Patents

Description

where Rs-RS has the indicated meanings, and the E-carboxyl group, or the corresponding ester of this group, or its salt, nitrile group, a group in the form of a halide acid or an amide group, is reacted with a base or salt, followed by isolation of the target product.

Compounds capable of converting group E to a salt of the carbonyl acid group are, for example, bases and ion exchange resins containing cations, for example sodium, potassium, ammonium and suitable nitrogen-containing organic cations. It is preferable to prepare the salts by treating the free acid of the formula I with an appropriate base, for example, an alkaline earth or alkali metal hydroxide, carbonate or bicarbonate in an aqueous solution or by an exchange method. When using a strong base, precautions must be taken, for example, keeping the temperature low enough so that the compound of formula I does not undergo hydrolysis or other degradation.

The salt can be isolated from the reaction mixture by the method of precipitating and / or removing the solvent by evaporation or drying by freezing.

In the examples given, quantities are given in parts by weight, molecular weights are determined using a Perkin-Elmer RMU6 mass spectrometer, NMR values are determined in deuterated dimethyl sulfo oxide (unless otherwise indicated), infrared spectrum is determined for potassium bromide disks .-- -I

Example 1. Patric salt of 8-allyl-5- (2oxypropoxy) -4-oxo-4H-1-benzopyran-2-carboxylic acid.

A solution of 1.7 parts of 8-allyl-5- (2-hydroxypropoxy) -4-oxo-4H-1-benzopyran-2-carboxylic acid hemihydrate and 0.42 parts of sodium bicarbonate is prepared in 25 parts of water. The resulting solution is filtered and freeze dried. Obtain 1.8 parts of the sodium salt of 8-allyl-5- (2oxypropoxy) -4-oxo-4P-1 - benzopyran-2-carboxylic acid.

Example 2. Patrician salt of 6,8-di-t / 7r-BUTYL-4-OXO-4P-1-benzopyran-2-carboxylic acid.

To 5.5 parts of 6,8-di-G; oet-butyl-4-oxo-4H-1-benzopyrene-2-carboxylic acid was added 1.4 parts of sodium bicarbonate in 150 vol. h of water. The mixture is gently heated on the steam bath until almost all the acid is dissolved. Peyralny solution is filtered and dried by freezing. The sodium salt of 6,8-dpt / 9-butyl-4-oxo-4H-1-benzopyran-2-carboxylic acid is obtained.

Example 3

a) Piperidine salt of 6,8-an-tert-butyl-4ОКСО-4Н-1 -benzopyran-2-carboxylic acid.

A solution of 5.0 parts of 6,8-di-treg-butyl-4-oxo-4P1-benzopyran-2-carboxylic acid in 1.7 hours

piperidine and 50 parts of water are filtered and freeze-dried. The resulting pale yellow powder was washed with hot petroleum ether (bp 60-80 ° C) and 5.6 parts of 5 piperidine salts of 6,8-di-tert-butyl-4-oxo4H-1-benzopyran-2 were obtained. -carboxylic acid in the form of a colorless powder with m. pl. (decomposition) 191 -194 ° C. Paideno,%: C 71.5; H 9.65; N 3.57.

10S2zNzMO4.

Calculated,%: C 71.29; P 8.56; N 3.61. NMR showed a 3-proton of the benzopyran ring as a singlet at 3.23 tons, and broad signals at 7.05 tons and 8.60 tons were attributed to 15 protons of the piperidine ring (the solvent is deuterium oxide).

b) Ethyl salt of 6,8-di-heated-butyl-4-oxo-4H-1-benzopyran-2-carboxylic acid.

5.0 parts of 6.8-di-greg-butyl-4-oxo-4H-1-benzopyran-2-carboxylic acid are added to the mixture 1.5 parts of 70% aqueous ethylamine and 50 parts of water . The resulting pale yellow solution is filtered and freeze dried. The resulting solid is washed with ether and 5.3 parts of the ethylamine salt of 6,8-di-treg-butyl-4-oxo-4P-1-benzopyran-2-carboxylic acid are obtained in the form of a colorless powder with mp. (decomposition) 205-206 ° C. Paydeno,%: C 69.2; H 8.72; N 3.74;

0C2oH29NO4.

Calculated,%: C 69.13; H 8.41; N 4.03.

The 3-proton of the beo-pyran ring gave a NMR singlet at 3.20 t, and the N-ethyl group gave a quartet at 7.00 t and a triplet at 8.80 t (dissolved 5% deuterium oxide).

Winner 4. Sodium salt of 6-allyl-5-hydroxy-4-OXO-4P-1-benzopyran-2-carboxylic acid.

A solution of 0.7 parts of 6-allyl-5-hydroxy-4-oxo-4H-10 benzopyran-2-carboxylic acid and 0.24 parts of sodium bicarbonate in 50 parts of water is freeze-dried to obtain 0.7 parts of sodium salts of 6-allyl-5-hydroxy-4-oxo-4P-1-benzopyrap-2carboxylic acid as a yellow solid

5 substances.

Example 5. Patric salt of 6,8-di-g; 7r-BUTYL-4-OXO-4P-1-benzopyran-2-carboxylic acid.

To a cooled solution of 1.02 hours ethyl

0 Ester 6,8-di-greg-butyl-4-oxo-4P-1-benzopyrap-2-carboxylic acid per 100 parts of ethanol was added 3.1 parts of 1N sodium hydroxide solution. The solution is stirred at room temperature for 1 hour, then the solvent

5 evaporated. The remaining solid is triturated with ether and filtered. The yield is 0.93 parts of sodium salt of 6,8-di-tert-butyl-4-oxo-4P-1-bezopyran-2-carboxylic acid.

Example 6. 5- (3-Methyl-n-butoxy) -8-n-propyl-4-oxo-4P-1-benzopyran-2-carboxylic acid.

a) 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4P-1 ethyl ester - benzopyran - 2-carboxylic

5 acid.

A solution of 53 parts of 8-allyl-5- (3-methyl-n-butoxy) 4-oxo-4H-1-benzopyran-2-carboxylic acid in 750 parts of ethanol containing 2.0 parts of concentrated sulfuric acid, bale t t with reflux for 20 hours. Ethanol is distilled off, and the solution of residual oil in chloroform is washed with an aqueous solution of sodium bicarbonate and water. The chloroform solution is then dried and extracted to an oil. This oil is dissolved in diethyl ether. On standing, 45 parts of 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-1-benzoniran-2-carboxylic acid ethyl ester are crystallized as yellow needles with so-called nl. 104- 106 ° C.

Found,%: C 69.70; H 7.22.

С2оН24О5.

Calculated,%: C 69.75; H 7.02.

Molecular weight 344 (determined by mass spectroscopy). NMR (in a CDCb solution) shows the protons of ethyl ether in the form of a quartet and a triplet at 5.63 tons and 8.62 tons, respectively.

b) 5- (3-Methyl-n-butoxy) -8-n-propyl-4-oxo4H-1-benzopyran-2-carboxylic acid.

A suspension of 12.05 parts of 8-allyl-5- {3-methyl-n-butoxy) -4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester in 225 parts of ethanol is hydrogenated under pressure of 4 atm using 5% palladium on charcoal as a catalyst. After 30 minutes the supply of hydrogen is stopped and the reaction mixture is filtered. The filter volume is reduced, and then water is added. On standing, yellow needles (10.2 parts) of 5- (3-methyl-n-butoxy) -8-c-propyl-4-oxo-4P-1-benzopyran-2-carboxylic acid ethyl ester fall out. pl. 64.5-65 ° C. This product is stirred for 2 hours with a hot sodium bicarbonate aqueous solution containing some ethanol. The resulting solution is cooled, washed with diethyl ether and acidified with dilute hydrochloric acid. The yellow precipitate is collected and crystallized from aqueous ethanol. 7.2 parts of 5- (3-methyl-n-butoxy) -8-n-propyl-4-oxo-4H1-benzopyran-2-carboxylic acid are obtained in the form of yellow needles with mp. 166-167 ° C.

Found,%: C 67.50; H 6.97.

CisHagOg.

Calculated,%: C 67.90; H 6.97.

Molecular weight 318 (determined by mass spectroscopy). The infrared spectrum shows absorption for carbonyl acid at 1740, and for carbonyl of the benzopyran ring, at 1640 NMR showed a 3-proton of the benzopyran ring as a singlet at 3.4t.

c) Sodium salt of 5- (3-methyl-n-butoxy) -8n-propyl-4-oxo-4H-1-benzopyran - 2-carboxylic acid.

A mixture of 4.77 parts of 5- (3-methyl-n-butoxy) -8-n-propyl-4-oxo-4H-1-benzonrane-2-carboxylic acid and 1.26 parts of sodium bicarbomate was dissolved in 100 h of water. The solution is filtered and freeze dried. As a result of crystallization from ethanol, 3.3 parts of a white hygroscopic solid are obtained, which is the sodium salt of 5- (3-methyl-n-butoxy) -8-c-propyl-4-oxo-4H-1 - benzopyran-2carboxylic acid.

The infrared spectrum shows a wide absorption band for carboxylate ion and is about 1070 cm.

NMR shows the 3-proton of the benzopyran ring as a singlet at 3.48 t.

Example 7. 6,8-Di-n-propyl-4-oxo-4H-1benzopyran-2-carboxylic acid. a) 6,8-Di-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid.

A solution of 6.2 parts of 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid in 100 parts of ethanol is hydrogenated at room temperature for 45 minutes at a pressure of 45 psig. inch in the presence of 5% palladium on coal. The solution is filtered and evaporated. Get 6,1 p. 6,8-di-n-propyl-4 - OXO-4H - 1-benzopyran-2carboxylic acid with so pl. 183-184 ° C after recrystallization from a mixture of ethyl acetate and petroleum ether (bp 60-80 ° C).

Found,%: C 70.0; H 6.75.

Cl6Hi804.

Calculated,%: C 70.05; H 6.61.

Molecular weight 274 (determined by mass spectrometry).

The absorption spectrum of the IR spectrum for carboxylic acid 1725, for benzopyrancarbonyl - 1620 cm -.

The NMR spectrum contains a singlet at 2.7t due to the 3-proton of the benzopyran ring (solvent is deuterochloroform).

b) Sodium salt of 6,8-di-n-propyl-4-oxo-4H-1-benzoiira-2-carboxylic acid.

A mixture of 4.7 parts of 6.8-di-n-propyl-4-oxo-4H-1benzopyran-2-carboxylic acid and 1.37 parts of sodium bicarbonate was dissolved in 50 parts of water. The filtered solution is freeze-dried and 4.5 grams of sodium salt are obtained.

6,8-di-n-propyl-4-oxo-4H - 1-benzopyran - 2carboxylic acid.

The absorption spectrum of the IR spectrum for carbonate is 1620 cm. The NMR spectrum showed a singlet at 3.3t due to the Z-proton of the benzopyran

rings (solvent - deuterium oxide).

Example 8. 5- (3-Methyl-n-butoxy) -4-oxo4H-1-benzopyran-2-carboxylic acid.

a) Tallium salt of ethyl 5-hydroxy-4-oxo-4H-1benzopyran-2-carboxylic acid.

A freshly prepared solution of 164.8 parts of ethyl acetate in 500 parts of chloroform is quickly added to a stirred solution of 160 parts of 5-OXY-4-OXO-4H-1-benzopyran-2-carboxylic acid in 2000 parts of chloroform. Add eh

1000 hours of chloroform and the mixture is stirred for 20 minutes. The cooled product is separated by filtration, washed with chloroform and dried. Receive 303 parts of thallium salt of ETHYL-5-OXY-4-OXO-4H-1 - benzopyran-2 carboxylate with m. Pl. above 300 ° C.

Example 9. 5- (3-Methyl-n-butosp) -4-oxo4H-1-benzopyran-2-carboxylic acid.

A mixture of 1.0 parts of 5- (3-methyl-n-butoxy) -4-oxo4H-1-benzopyran-2-carbonitrile, 20 parts of dioxane, and 20 parts of dilute hydrochloric acid is heated under reflux for 24 hours . The dioxane is extracted, the reaction mixture is extracted with chloroform. The chloroform layer is then extracted with a saturated solution of sodium bicarbonate, from which, after acidification, 0.30 parts of 5- (3-methyl-α-butoxy) -4-oxo-4H-1-benzopyra-2-carboxylic acid are obtained with a t. 180-182 ° C. The point of indexing, IR spectra and chromatography in a thin layer of the product obtained are identical to the corresponding properties of the compound obtained in the sample 8.

Example 10. 6,8-Diproyl-4-oxo-4H-1-benzopyran-2-carboxylic acid.

A mixture of 1.0 parts of 6,8-dipropyl-4-oxo-4H-1-beisopira-2-carboxamide, 20 parts of glacial acetic acid and 20 parts of a solution of hydrogen bromide (45% w / v) in glacial acetic acid was heated under reflux for 3 hours, then water was poured and extracted with chloroform. Extraction of the organic layer with a saturated solution of sodium bicarbonate and subsequent acidification of the bicarbonate layer yields 0.16 parts of 6.8-dipropyl-4-oxo-4H-1-benzopyran-2-carboxylic acid with m.p. 183-184 ° C (decomposition). The melting point, IR spectrum and chromatography in a thin layer of the material obtained are identical to the corresponding properties of the compound obtained in Example 7.

Example 11. 8-Allyl-5- (3-methyl-n-butoxy) -4-oxo-4P-1-benzopyran-2-carboxylic acid.

To a solution of 5.0 parts of 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-1-benzopyran-2-carbonyl chloride in 50 parts of dichloroethane is added with stirring 10 parts of water. The mixture is stirred at 50 ° C for 1 hour and then evaporated to dryness. The resulting solid was carefully stained with an aqueous solution of sodium bicarbonate. As a result of acidifying the bicarboate solution with concentrated hydrochloric acid, a yellow precipitate is formed. The precipitate is crystallized from ethyl acetate and obtain 2.6 parts of 3-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-1Zenopyran-2-carboxylic acid with mp. 198-199 ° C.

Example 12. The hydroxylamine salt of 5- (3-methyl-n-butoxy) - 4-OXO-4H-1 - benzopyran-2-carboxylic acid.

An alkaline solution of hydroxylamine is obtained by mixing 4 parts of sodium bicarbonate with 3.6 hours. hydroxylamine hydrochloride per 100 hours of this heated with a reverse refrigeration; after 15 minutes, the resulting precipitate of sodium chloride is filtered.

To a stirred suspension of 5 parts of 5- (3-megyl-n-butoxy) -4-oxo-4H-1-benzocyran-2 arbonic acid in 50 parts of ethanol, heated under reflux, are added

40 h hydroxylaminobugo filtrate. The mixture was agitated and heated under reflux for another 15 minutes, and then allowed to cool. The white solid is filtered and 5 parts of the 5- (3-methyl-n-butoxy) -4-oxo-4H-1-benzoi-2-carboxylic acid hydroxylamine salt are obtained. Found,%: C 57.89; H 6.18; N 4.46. CjsHigNOe. Calculated,%: C 58.24; H 6.19; N 4.53.

Example 13. The ethylamine salt of 8-allyl-5 (3-methyl-n-butoxy) -4-oxo-41-1 - 1-benzopyran-2-carboxylic acid.

An aqueous solution containing 5 parts of 8-allyl 5- (3-methyl-n-butoxy) -4 - OXO-4P-1 - benzoirane-2-carboxylic acid and 1.07 parts ethyl lamp

(70% of the volume), filtered and freeze-dried. 5 parts of ethylamine salt of 8-allyl-5- (3-methyl-n-butoxy) 4-oxo-4H-1-benzoiran-2-carboxylic acid are obtained.

as a light yellow solid with

m.p. 135-137 ° C.

Found,%: C 64.35; H 7.37; N 3.48.

С2оП27М05-1 / 2Н20.

Calcd.,%: C 64.90; P 7.57; N 3.79.

Example 14. 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-1-beisopyra-2-carboxylic acid piheride salt.

A solution of 5 parts of 8-allyl-5- (3-methyl-n-butoxy) 4-oxo-4H-1-beisoieran-2-carboxylic acid and 1.35 parts of piperidine in 50 parts of ethanol is heated under reflux 2 hour. The solution obtained is filtered and evaporated to an oily residue, which is dissolved in dry benzene. The benzene solution is distilled and an oil is obtained, which is triturated with tertiary ether (m.p. 40. BOC). Get 6 hours of the iiperidine salt of 8-allyl-5- (3methyl-n-butoxy) -4 - oxo-4H-1-beisopyran-2carboxylic acid in the form of a solid product Art. square 106-107 ° C. Found,%: C 68.81; H 7.78; N 3.49. Crznzgmoz.

Calculated,%: C 68.59; H 7.77; N 3.30. Example 15. The calcium salt of 8-allyl-5- (3methyl-n-butoxy) -4-oxo - 4H-1-benzopyran-2carboxylic acid.

To a solution of 4.93 g of sodium salt of 8-allyl-5 (3-methyl-n-butoxy) -4-oxo-4H-1-benzopyran-2-carboxylic acid in 50 parts of water is added a saturated solution of 1.2 parts of nitrate calcium in water. The resulting calcium salt is filtered, washed with water and dried. 5 parts of myohydrate of the calcium salt of 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-1-benzopyran-2-carboxylic acid are obtained in the form of a solid product.

Found,%: C 62.89; H 5.91. SzbNzSaOuNgO. Calculated%: C 62.80; H 5.82.

Example 16. Three- (hydroxymethyl) -met1 laminic salt of 8-allyl-5- (3-methyl-n-butoxy) -4-oxo4H-1-benzopyran-2-carboxylic acid.

A solution of 5.66 parts of 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-benzopyran - 2-carboxylic acid9

Slots 1: 2.16 parts of tri- (oxymethyl) -methylamine. 50 parts of ethanol are heated under reflux for 2 hours. The solution is filtered and evaporated to an oily residue, which is dissolved with ether. The trn (ox-methyl) -methylamine salt of 8-allyl-5 (3-methyl-n-butoxy) -4-oxo-4H-1-benzoniran-2-carboxylic acid hemihydrate is obtained as a pale yellow yellow solid.

Found,%: C 59.52; H 7.43; N 3.06.

С2оНз1МОз-1 / 2Н20.

Calculated,%: C 59.20; H 7.18; N 3.14.

Example 17. (p-Diethylamino) ethyl ester.

6.8-di-g / er-but-11l-4-oxo-4P-1 - benzonrane 2-carboxylic acid hydrochloride.

A mixture of 10 parts of the sodium salt of 6,8-di-t / 7r-butyl-4-OXO-4P - 1-benzonir-2-carboxylic acid and 8 parts of (p-diethylamino) -ethyl chlorohnd was shaken for 1 hour in beizole, and then 10 hours heated under reflux. After cooling, the inorganic solid precipitate is filtered, and the filtrate is left to an oily residue, which is kept for 3 hours at 110 ° C and a pressure of 15 mm Hg. Art. to remove the residue (| 3-diethylamino) ethyl chloride. The oil is then dissolved in diethyl ether, and an ethereal solution of hydrogen chloride is added to this solution. The resulting solid product is filtered and crystallized from a mixture of dioxane and diethyl ether. 7.01 parts of hydrochloride (p-diethylamino) ethyl ester of 6,8-di-tert-butyl-4-OXO-4P-1-benzonran-2-carboxylic acid are obtained in the form of a white solid venous1.

Found,%: C 64.91; H 8.23; N 3.09.

С24НзбС1М04-1 / 2Н, О.

Calculated,%: C 64.50; H 8.06; N 3.14.

Example 18. Hydrochloride (p-diethylamino) ethyl ester of 8-allyl-5- (3-methyl-n-butoxy) -4-oxo - 4H-1-benzoiran-2 - carboxylic acid.

A mixture of 10.14 parts of sodium salt of 8-allyl-5- (3methyl-n-butoxy) -4 - oxo-4H-1-benzonaran-2-carboxylic acid and 8.13 parts of (p-diethylaminio) ethyl chloride is heated in benzene with reflux for 10 hours. The inorganic product is filtered and the filtrate is evaporated in vacuo to an oil. The oil is heated for 3 hours at 110 ° C and at a pressure of 15 mm Hg. Art. in order to remove traces of (p-diethylaminio) ethyl chloride. The residual oil is cooled and dissolved in diethyl ether. An ethereal solution of hydrogen chloride is added to this solution. The resulting solid is filtered and crystallized from a mixture of dioxane and diethyl ether. 9.8 parts of hydrochloride (p-diethylamino) ethyl are obtained, 8-allyl-5- (3-methyl-n-butoxy) -4oxo-4H-1-benzopyran-2-carboxylic acid hemihydrate is obtained in the form of a white solid. with t. pl. 125 ° C.

Found,%: C 61.67; H 7.50; N 3.02.

C24H34C1N05-1 / 2H20.

Calculated,%: C, 61.95; H 7.60; N 3.04.

ten

The structure is confirmed by NMR and mass spectroscopy.

Example 19. 8-Allyl-5- (3-methyl-n-butoxy) -4-oxo-2H-1-benzopyra-2-carboxylic acid hydrochloride 2-dimethylamine-2-yl ester.

To a suspension of 6.76 parts of sodium salt of 8-allyl 5- (3-methyl-n-butoxy) -4-oxo-4H-1-benzopyran-2-carboxylic acid in 200 parts of dry benzene was added 5.42 parts. 2-chloro-2-dimethylammethyl propane. The mixture is heated under reflux for 10 hours, cooled and filtered. The filtrate is evaporated to an oil, which is dissolved in diethyl ether.

The ether solution is filtered and left to form an oil, which is then maintained at 100 ° C under vacuum for 6 hours. After dissolving in ether, an excess of an ethereal solution of hydrogen chloride is added to the oil. The resulting solid is 4 parts of 2-dimethylamiomethylprop-2-yl ester 8-allyl-5- (3-methyl-n-butoxy) -4-oxo-4H-1-benzoiran-2carboxylic acid hydrochloride hydrate. After washing with ether

and crystallization of ns benzene, the product is a harder substance with m.p. 183-184 ° C. Found,%: C 61.75; H 8.04; N 2.82.

C24H34C1N05-H20.

Calculated,%: C 61.4; H 7.67; N 2.98.

The structure is confirmed by NMR and mass spectroscopy.

Claims (1)

Invention Formula Method for preparing salts of 4-oxo-4H-1-beisopyran-2-carboxylic acid of the formula 40 Cun where Rs is a hydrogen atom, hydroxy group or The OR5 group, where -Rs is a linear or branched, ethylenically unsaturated or ethylenically linked hydrocarbon group, which can be replaced by a hydroxy group or five- or six-membered oxygen-containing heterocyclic ring, and Rs together with any substituents may contain 3-8 atoms carbon; Re -: a hydrogen atom, alkyl with 1-6 carbon atoms, alkannl with 2-6 carbon atoms or phenyl; Ry is a hydrogen atom or a (lower alkoxn) lower alkoxy group; Re is a hydrogen atom, alkyl with 1-6 carbon atoms or alkenyl with 2--6 carbon atoms and iri provided that 1) Rs does not mean propyl when R5 is an oxypropoxy group; 2) Rs does not mean ethyl when Rs is a but-3-enoxyl group; 3) two or three of the radicals Rs-Rs do not mean a hydrogen atom, except when a) Rs is alkyl or alkenyl with eleven straight chained with 5-7 carbon atoms or branched chain alkyl or alkoyl having 6-8 carbon atoms, then none, one or two of the radicals Rg-Rs are hydrogen atoms or b) Re is phenyl, then none , one or two of the radicals R and Rs are not a hydrogen atom; 4) Re and Rg are both ethyl or both secondary butyl, only when Rs does not mean a hydrogen atom; 5) Re is alkyl with 4-6 carbon atoms, when Rr is (lower alkoxy) -low alkoxy, and 6) at least one of the Re and Rs radicals contains two n more carbon atoms, if Rs is a hydrogen atom or an oxy group, characterized in that the formulas Rr o ABOUT. where the RS-Rs have the indicated meanings, and the E-carboxyl group, or the corresponding ester of this group, or its salt, nitrile group, halogenation as a halide acid, or amide group, is reacted with a base or salt, followed by isolation of the desired product. Priority featured: 08.25.70 at Rs - a hydrogen atom or a hydroxy, hydroxypropoxy or 3-methyl-m-butoxy group; Re is a hydrogen atom or an alkyl or alkeyl with 2-6 carbon atoms; Ry is a hydrogen atom or a (lower alkoxy) -low alkoxy group; Rs is a hydrogen atom or an alkyl or alkenyl with 2-6 carbon atoms, except for c-propyl; moreover, RS is alkenyl, when Rs is a hydroxypropoxy group and two or three of the radicals Rs-Rs do not mean a hydrogen atom, except for the case when Rs is a 3-methyl-n-butoxy group. 12 11.12.70 when RS is an alkoxy group with a branched chain with 5-8 carbon atoms or a tetrahydrofurfuryloxy group; Re is a hydrogen atom or an alkyl or alkenyl with 2-6 carbon atoms; R / is a hydrogen atom or a (lower alkoxy) -low alkoxy group; Rs is a hydrogen atom, alkyl or alkenyl with 2-6 carbon atoms, in addition to n-propyl; moreover, Rs alkeiil, when Rs is hydroxypropoxy and 0 two or three of the radicals Rs-Rs do not mean a hydrogen atom, except for the case when Rs is a branched chain alkoxy group with 5-8 carbon atoms, then one, two or three of the radicals Rs-Rs may not mean 5 hydrogen atom; Re and Rs are ethyl when RS is hydroxy. 03.06.71 when RS is a hydrogen atom, hydroxy group or group ORs, where Rs is an ir or branched saturated or ethylenically unsaturated hydrocarbon group with 3-8 carbon atoms, unsubstituted or substituted with an oxy group or a six or six membered oxygen-containing heterocyclic ring; Rg is a hydrogen atom, 5 alkyl with 1-6 carbon atoms or alkenyl with 2-6 carbon atoms; RT is a hydrogen atom or a lower alkoxy lower alkoxy group; RS is a hydrogen atom, alkyl with 1-b carbon atoms or alkenyl with 2-6 carbon atoms, provided that 1) Rs cannot mean ethyl, when RS is a but-3-enoxyl group; 2) Rs is alkenyl, when Rs is hydroxyproioxy; 3) two or three of the radicals Rs-Rs do not mean a hydrogen atom except in the case 5 when Rs is a straight chain alkyl or alkenyl of 5-7 carbon atoms or a branched alkyl or alkenyl of 6-8 carbon atoms; 4) Re and Rs are both ethyl or secondary butyl when RS is not a hydrogen atom; 0 5) Re is alkyl with 4-6 carbon atoms if (lower alkoxy) is a lower alkoxy group and 6) at least one of the Re and Ra radicals contains two or more carbon atoms if RS is a hydrogen atom or an hydroxy group.