SU245100A1 - METHOD FOR PREPARING SUBSTITUTE ALKINYL ESTERS OF PYROCATEXINPHOSPHORIC ACID - Google Patents
METHOD FOR PREPARING SUBSTITUTE ALKINYL ESTERS OF PYROCATEXINPHOSPHORIC ACIDInfo
- Publication number
- SU245100A1 SU245100A1 SU1224805A SU1224805A SU245100A1 SU 245100 A1 SU245100 A1 SU 245100A1 SU 1224805 A SU1224805 A SU 1224805A SU 1224805 A SU1224805 A SU 1224805A SU 245100 A1 SU245100 A1 SU 245100A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- pyrocatexinphosphoric
- minus
- alkinyl
- esters
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N Propargyl alcohol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 2
- KXOHONQCPYDQTC-UHFFFAOYSA-N chloro(dioxido)phosphane Chemical compound [O-]P([O-])Cl KXOHONQCPYDQTC-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 2
- FKXIKZFKAILXMF-UHFFFAOYSA-N benzene-1,2-diol;phosphorous acid Chemical compound OP(O)O.OC1=CC=CC=C1O FKXIKZFKAILXMF-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- -1 alkynyl ethers Chemical class 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N Catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- 229940100626 Catechin Drugs 0.000 description 1
- 229950001002 Cianidanol Drugs 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930016253 catechin Natural products 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910000050 copper hydride Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
;1;one
Изобретение касаетс способа получени неописанных алкиниловых эфиров пирокатехинфосфористой КИСЛОТЫ общей формулыThe invention relates to a process for the preparation of undescribed alkynyl ethers of pyrocatechin phosphorous acid, of the general formula
РОСНгС СХ О/ROSNGS CX O /
где XSiRs, -CH-jNRa, -Cl и др.where XSiRs, -CH-jNRa, -Cl, etc.
Соединени этого типа могут найти применение в синтезе физиологически активных веществ , в качестве экстрагентов, пластификаторов ДЛЯ полимеров.Compounds of this type can be used in the synthesis of physiologically active substances, as extractants, plasticizers FOR polymers.
Предложенный способ основан на взаимодействии пирокатехинхлорфосфита с узамещенным пропаргилоБЫм спиртом при охлаждении до минус 10 - минус 50°С. Реакцию ведут в инертном органическом растворителе в присутствии органического основани , например триэтиламина.The proposed method is based on the interaction of pyrocatechin chlorophosphite with a highly substituted propargyl alcohol when cooled to minus 10 - minus 50 ° C. The reaction is carried out in an inert organic solvent in the presence of an organic base, for example triethylamine.
В ИК-спектре синтезированных веществ имеетс полоса поглощени 2180 см, характерна ДЛЯ двузамещенной ацетиленовой группы .In the IR spectrum of the synthesized substances, there is an absorption band of 2180 cm, characteristic of the disubstituted acetylene group.
Пример 1. Получение у-триметилсилилпропинилового эфира пирокатехинфосфористойExample 1. Getting y-trimethylsilyl ether pyrocatechinphosphorous
прерывном перемешивании и температуре минус 50°С смесь 25,6 г триметилсилил-3-пропинил-2-ола-1 и 20,4 г триэтиламина в 50 мл абсолютного эфира. После прикапывани реакционную смесь перемешивают еще 2 час и оставл ют на ночь. На следующий день сол нокислый триэтиламин отфильтровывают, эфир отгон ют. Оставшеес светло-желтое масло перегон ют в вакууме. Получают 42,7 г (81,6% от теоретического) продукта. Т. кип. 117- 119°С при 1,5 мм рт. ст., 1,5182.discontinuous stirring and at a temperature of minus 50 ° C, a mixture of 25.6 g of trimethylsilyl-3-propynyl-2-ol-1 and 20.4 g of triethylamine in 50 ml of absolute ether. After the addition, the reaction mixture is stirred for another 2 hours and left overnight. The next day, triethylamine hydrochloride is filtered off and the ether is distilled off. The remaining light yellow oil is distilled under vacuum. Obtain 42.7 g (81.6% of theoretical) of the product. T. Kip. 117-119 ° C at 1.5 mm Hg. Art., 1.5182.
Найдено, %: С 54,79, 53,56; Н 5,44, 6,06; Р 11,73, 11,97.Found,%: C 54.79, 53.56; H 5.44, 6.06; R 11.73, 11.97.
CiaHisOgPSi.CiaHisOgPSi.
Вычислено, %: С 54,11; Н 5,67; Р 11,63.Calculated,%: C 54.11; H 5.67; R 11.63.
Пример 2. Получение со-диэтиламИнобутинилового эфира пирокатехинфосфористой кислоты .Example 2. Preparation of co-diethyl Inobutinyl pyrocate catechin phosphorous acid.
к 34,9 г пирокатехинфосформонохлорида в 700 мл абсолютного эфира прикапывают при непрерывном перемешивании и температуре минус 50°С смесь 28,2 г 4-диэтиламинобутин-2ола-1 и 20,4 г триэтиламина в 50 мл абсолютного эфира. После прикапывани реакционную смесь перемешивают 2 час и оставл ют на ночь. На с тедующий день сол нокислый триэтиламин отфильтровывают, эфир отгон ют. Остаток представл ет собой зеленоватое масПолучают 53 г (96% от теоретического) продукта-сырца .To a mixture of 28.2 g of 4-diethylaminobutin-2ola-1 and 20.4 g of triethylamine in 50 ml of absolute ether, was added dropwise to 34.9 g of pyrocatechol phosphormonochloride in 700 ml of absolute ether with continuous stirring at minus 50 ° C After the addition, the reaction mixture is stirred for 2 hours and left overnight. On the following day, triethylamine hydrochloride is filtered off and the ether is distilled off. The remainder is greenish. 53 g (96% of theoretical) of the crude product are obtained.
Найдено, %: С 60,04, 60,34; Н 6,64, 6,23; N4,92, 5,15; Р 11,47, 11,23.Found,%: C 60.04, 60.34; H 6.64, 6.23; N4.92, 5.15; R 11.47, 11.23.
CuH.gOsPN.CuH.gOsPN.
Вычислено, %: С 60,2; Н 6,49; N 5,01; Р 11,1.Calculated,%: C 60.2; H 6.49; N 5.01; R 11.1.
Предмет изобретени Subject invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU245100A1 true SU245100A1 (en) |
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