SU784773A3 - Method of preparing monoacetoxyethylenecarbonate - Google Patents

Method of preparing monoacetoxyethylenecarbonate Download PDF

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Publication number
SU784773A3
SU784773A3 SU752134772A SU2134772A SU784773A3 SU 784773 A3 SU784773 A3 SU 784773A3 SU 752134772 A SU752134772 A SU 752134772A SU 2134772 A SU2134772 A SU 2134772A SU 784773 A3 SU784773 A3 SU 784773A3
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SU
USSR - Soviet Union
Prior art keywords
carbonate
acetic acid
formula
monoacetoxyethylenecarbonate
preparing
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Application number
SU752134772A
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Russian (ru)
Inventor
Ре Лючиано
Бассигнани Лючиано
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Снампрогетти С.П.А. (Фирма)
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Publication of SU784773A3 publication Critical patent/SU784773A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1503772 Monoacyloxyalkylene carbonate SNAMPROGETTI SpA 15 May 1975 [17 May 1974] 20709/75 Heading C2C A monoacyloxyalkylene carbonate of formula where R is a hydrocarbyl radical, and R 1 and R 2 , the same or different, are hydrocarbyl radicals or hydrogen, e.g. monoacetoxyethylene carbonate, is prepared by reacting where Y is halogen, with an alkali or alkaline earth metal salt of an acid R.COOH in the presence of the acid.

Description

Изобретение относитс  к способу получени  нового соединени  формулы которое может найти применение в синтезе fi-оксиаминокислот. Способ основан на известной в органической химии реакции взаимодействи  галогенсодержащего соединени  например п-нитробензилхлорида с солью уксусной кислоты и щелочного металла , например ацетата натри  в ере де уксусной кислоты с последующим получением п-нитробензилового эфира уксусной кислоты l . .Цель изобретени  - получение нового соединени  - моноацетоксиэтилен карбоната, которое  вл етс  промежуточньлм продуктом в синтезе -оксиаминокислот . Эта цель достигаетс  тем, что соединение формулы. где У - атом галогена, подвергают взаимодействию с солью уксусной кислоты и щелочного или щелочноземельного металла при температуре кипени  реакционной среды в присутствии уксусной кислоты. Пример 1. Получение моноацетоксиэтиленкарбоната . В 100мл лед ной уксусной кислоты внос т 9,19 г (75 моль) монохлорэтиленкарбоната , 7,36 г (75 моль) безводного уксуснокислого кали  и смесь нагревают при температуре кипени  (с обратньам холодильником) 15 ч, при перемешивании, без доступа атмосферной влаги. Газохроматографический анализ (внутренний стандарт, этиленкарбонат) указывает на 95%-ный выход моноацетоксиэтиленкарбоната . Реакционную смесь при комнатной температуре отфильтровывают от солей, осадок промывают бензиловым эфиром, объединенные фильтраты упаривают под вакуумом в ротационном испарителе до половины объема. Приливают двойной объем этилового эфира дл  осаждени  остаточ;ных солей, их отфильтровывают и промывают этиловым эфиром. ОбъединенныеThe invention relates to a process for the preparation of a novel compound of the formula which can be used in the synthesis of fi-hydroxy amino acids. The method is based on the reaction of reacting a halogen-containing compound, known in organic chemistry, for example p-nitrobenzyl chloride with a salt of acetic acid and an alkali metal, for example sodium acetate in an acetic acid potassium, followed by obtaining acetic acid p-nitrobenzyl ester l. The purpose of the invention is to obtain a new compound, mono acetoxyethylene carbonate, which is an intermediate product in the synthesis of α-hydroxy amino acids. This goal is achieved by the compound of the formula. where Y is a halogen atom, is reacted with an acetic acid salt and an alkali or alkaline earth metal at the boiling point of the reaction medium in the presence of acetic acid. Example 1. Obtaining monoacetoxyethylene. 9.19 g (75 mol) of monochlorethylene carbonate, 7.36 g (75 mol) of anhydrous potassium acetate are added to 100 ml of glacial acetic acid and the mixture is heated at boiling point (with reflux condenser) for 15 h, with stirring, without access of atmospheric moisture . Gas chromatographic analysis (internal standard, ethylene carbonate) indicates a 95% yield of mono acetoxyethylene carbonate. The reaction mixture at room temperature is filtered off from the salts, the precipitate is washed with benzyl ether, the combined filtrates are evaporated under vacuum in a rotary evaporator to half the volume. Double volume of ethyl ether is added to precipitate the residual salts, they are filtered and washed with ethyl ether. United

фильтраты вновь упаривают под вакуумом в ротационном испарителе до образовани  масл нистого остатка, который очищают дистилл цией, моноацетоксиэтиленкарбонат , перегон етс  при 132-134С/3 мм рт.ст. (172°С в бане), оставл   значительный углеродистый остаток в бойлере.the filtrates are again evaporated under vacuum in a rotary evaporator until an oily residue is formed, which is purified by distillation, the mono acetoxyethylene carbonate is distilled at 132-134 ° C / 3 mm Hg. (172 ° C in the bath), leaving a significant carbon residue in the boiler.

Получают 5,50 г вещества (густое масло).5.50 g of substance are obtained (thick oil).

ИК-спектр (пленка): макс. 1820 ( карбоната), 1758 ( ацетата ), 1230 ( ацетата) 1160, 1090, 995 ( карбоната).IR spectrum (film): max. 1820 (carbonate), 1758 (acetate), 1230 (acetate) 1160, 1090, 995 (carbonate).

Claims (1)

1. Способ получени  моноацетокснэтиленкарбоната формулы1. A method of producing monoacetoxy ethylene carbonate of formula ОСОСНзOOSNz (1)(one) ss IIII о .about . отличающийс different   тем, что соединение формулыthe fact that the compound of the formula Щ)U) где У - атом галогена, подвергают взаимодействию с солью уксусной кислоты ищелочного или щелочноземельно го металла в присутствии уксусной кислоты при температуре кипени  реакционной среды.where Y is a halogen atom, is reacted with an acetic acid salt of an alkali metal or alkaline earth metal in the presence of acetic acid at the boiling point of the reaction medium. Источники информации,Information sources, прин тые во внимание при экспертизеtaken into account in the examination 1. Хартмэн В., Рарс Э. Синтезы органических препаратов. М., ИЛ, 1952, сб. 3, с. 351.1. Hartman V., Rars E. Synthesis of organic drugs. M., IL, 1952, Sat. 3, s. 351.
SU752134772A 1974-05-17 1975-05-16 Method of preparing monoacetoxyethylenecarbonate SU784773A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT22874/74A IT1012483B (en) 1974-05-17 1974-05-17 PROCESS FOR THE PREPARATION OF MO NO ACYLOXES OR AROYL OXES ALCYLEN CARBONATES AND OBTAINED PRODUCTS

Publications (1)

Publication Number Publication Date
SU784773A3 true SU784773A3 (en) 1980-11-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
SU752134772A SU784773A3 (en) 1974-05-17 1975-05-16 Method of preparing monoacetoxyethylenecarbonate

Country Status (19)

Country Link
JP (1) JPS51110568A (en)
BE (1) BE829048A (en)
CA (1) CA1042906A (en)
CH (1) CH605901A5 (en)
CS (1) CS189592B2 (en)
DD (1) DD120876A5 (en)
DE (1) DE2521508A1 (en)
DK (1) DK216775A (en)
FR (1) FR2271223B1 (en)
GB (1) GB1503772A (en)
HU (1) HU172188B (en)
IL (1) IL47142A0 (en)
IT (1) IT1012483B (en)
LU (1) LU72494A1 (en)
NL (1) NL7505834A (en)
NO (1) NO751704L (en)
SE (1) SE418614B (en)
SU (1) SU784773A3 (en)
ZA (1) ZA753165B (en)

Also Published As

Publication number Publication date
IL47142A0 (en) 1975-07-28
HU172188B (en) 1978-06-28
CH605901A5 (en) 1978-10-13
BE829048A (en) 1975-09-01
LU72494A1 (en) 1975-08-28
GB1503772A (en) 1978-03-15
DD120876A5 (en) 1976-07-05
SE418614B (en) 1981-06-15
NO751704L (en) 1975-11-18
DK216775A (en) 1975-11-18
CA1042906A (en) 1978-11-21
JPS51110568A (en) 1976-09-30
CS189592B2 (en) 1979-04-30
FR2271223B1 (en) 1978-06-09
ZA753165B (en) 1976-04-28
SE7505617L (en) 1975-11-18
AU8104175A (en) 1976-11-18
DE2521508A1 (en) 1975-11-20
FR2271223A1 (en) 1975-12-12
JPS5519220B2 (en) 1980-05-24
NL7505834A (en) 1975-11-19
IT1012483B (en) 1977-03-10

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