SU305645A1 - METHOD OF OBTAINING DERIVATIVES OF BENZOIL-3-HAIR DRYER OR ACETIC ACID - Google Patents
METHOD OF OBTAINING DERIVATIVES OF BENZOIL-3-HAIR DRYER OR ACETIC ACIDInfo
- Publication number
- SU305645A1 SU305645A1 SU1296199A SU1296199A SU305645A1 SU 305645 A1 SU305645 A1 SU 305645A1 SU 1296199 A SU1296199 A SU 1296199A SU 1296199 A SU1296199 A SU 1296199A SU 305645 A1 SU305645 A1 SU 305645A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzoil
- acetic acid
- hair dryer
- solution
- obtaining derivatives
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title 3
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic Effects 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Description
Изобретение касаетс получени новых производных бензоил-3-фенилуксусной кислоты (оитических изомеров) общей формулыThe invention relates to the preparation of new benzoyl-3-phenylacetic acid derivatives (oitic isomers) of the general formula
СИ-СООНCOOH
где R - алкильный радикал, содержащи 1-4 атома углерода.where R is an alkyl radical containing 1-4 carbon atoms.
Предлагаемые вещества обладают фармакодинамическими свойствами, они чрезвычайно эффективны как противовоспалительные средства. Изомеры и вещества общей формулы (1), а также соответствующие рацематические вещества лмогут быть получены путем окислени соединени общей формулыThe proposed substances have pharmacodynamic properties, they are extremely effective as anti-inflammatory drugs. The isomers and substances of general formula (1), as well as the corresponding racemic substances, can be obtained by oxidizing a compound of general formula
/ 4-CH2-/VcH-COOH (2)/ 4-CH2- / VcH-COOH (2)
V RV r
где R - имеет указанное значение, перманганатом кали в щелочной среде при 20°С с последующим выделением целевого продукта известными приемами.where R - has the specified value, potassium permanganate in an alkaline medium at 20 ° C, followed by separation of the target product by known methods.
преобразованы в солп металлов или в соли с примесью азотированного основанн с помощью известных методов.converted to metal or metal salts with an admixture of nitrated based using known methods.
П р i м е р 1. Готов т раствор 10 г L-2-(3бензплфенил )пропионовой кислоты в 200 мл 1 и. едкого натра. Приливают 26 г раствора пермангапата калн в 800 мл воды. Смесь перемешивают 16 час при 20°С. затем подкисл ют 40 мл коицеитрпрованной серной кислоты , прпливают 80 м.л раствора бисульфата патри (уд. в. 1,24) и экстрагируют 800 мл хлористого лгетилена. Хлорпстометиленовый раствор промывают 200 мл воды и сущат над безводньп сульфатом натри , упаривают досуха в вакууме (20 мм рт. ст.) и получаюг 10 г желтого масла.Example 1. Prepare a solution of 10 g of L-2- (3-benzphenyl) propionic acid in 200 ml 1 and. caustic soda. 26 g of a solution of Kalnmanaphapat solution are poured into 800 ml of water. The mixture is stirred for 16 hours at 20 ° C. Then 40 ml of co-citrated sulfuric acid are acidified, 80 ml of a solution of patisulfate (sp. 1.24) are added to the solution and extracted with 800 ml of legitenum chloride. The chloropstomethylene solution was washed with 200 ml of water and dissolved over anhydrous sodium sulphate, evaporated to dryness under vacuum (20 mm Hg), and 10 g of yellow oil was obtained.
Масло раствор ют в 300 мл этилового эфира и эфирный раствор экстрагируют 200 м.л 1 и. раствора едкого натра. Водиый раствор подкисл ют 20 мл 12 п. сол иой кислоты, выдел етс масло. Экстрагируют 300 мл хлористого метилена, сушат над безводным сульфатом натри , упаривают досуха в вакууме (20 мм рт. ст. и получают 5,8 г желтого масла . Продукт очищают перекристаллизацией из смеси 17 мл окиси изопропила (изопропплоксид ) и 15 мл петролейного эфира (т. кип. 40-65°С). Получают 3 г 1-2-(3-бензоплфеН11л )проппоновой кислоты, т. нл 72 С (а) (а)5- 90---1,5°.The oil is dissolved in 300 ml of ethyl ether and the ether solution is extracted with 200 ml of l 1 and. caustic soda solution. The aqueous solution is acidified with 20 ml of 12 p. Hydrochloric acid and an oil is liberated. Extracted with 300 ml of methylene chloride, dried over anhydrous sodium sulfate, evaporated to dryness in vacuo (20 mm Hg. Art., And 5.8 g of a yellow oil is obtained. The product is purified by recrystallization from a mixture of 17 ml of isopropyl oxide (isoproploxide) and 15 ml of petroleum ether ( m.p. 40-65 ° C). Receive 3 g of 1-2- (3-benzophosphine 11l) proponic acid, t.nl 72 C (a) (a) 5- 90 - 1.5 °.
Пример 2. Опыт ведут по примеру 1, но с раствором 1,75 г )L-2-(3-бeнзилфeнил)пpoпиоиовой кислоты в 34,5 мл 0,1 г едкого натра и 15 мл дистиллированной воды и раствором 4,62 г перма пганата кали в 50 мл дпс1илл11 )ова1111оГ| воды, получают 0,73 t D/--2 (З-бопзонлфснпл)пропноновой кислоты, пла1иицсйс при 86°С.Example 2. Experience carried out according to example 1, but with a solution of 1.75 g) L-2- (3-benzylphenyl) propanoic acid in 34.5 ml of 0.1 g of sodium hydroxide and 15 ml of distilled water and a solution of 4.62 g perma of potassium pganate in 50 ml of dps1ill11) ova1111G | water, get 0,73 t D / - 2 (W-bozonolfsnpl) propnonic acid, platiiutsys at 86 ° C.
Предмет изобретени Subject invention
Способ нолучеии производных бензоил-3фенилуксусиой кислоты общей формулыMethod for the formation of benzoyl-3-phenyl-acetic acid derivatives of the general formula
со-/ -сн-соонco / -sn-soon
t/it / i
где R - алкил с 1-4 атомами углерода, например L-2-(3-бeизoилфeиил)нропноновпи кислоты, отличающийс тем, что вещества общей формулыwhere R is alkyl with 1-4 carbon atoms, for example, L-2- (3-beisoylfeiyl) nropnonovipic acid, characterized in that the compounds of the general formula
-CH2-Y YCH-COOH J R-CH2-Y YCH-COOH J R
где R имеет указанное значение, например L - 2-(3-бензилфенил)пропионовую кислоту, окисл ют в щелочной среде перманганатом кали с последующим выделеиием целевого продукта известиыми приемами.where R has the indicated value, for example, L-2- (3-benzylphenyl) propionic acid, is oxidized in an alkaline medium with potassium permanganate, followed by isolation of the target product with lime techniques.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU305645A1 true SU305645A1 (en) |
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