SU824892A3 - Способ получени производных феноксипропионовойКиСлОТы - Google Patents

Способ получени производных феноксипропионовойКиСлОТы Download PDF

Info

Publication number: SU824892A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mol; water; acid; general formula; solution
Prior art date: 1976-08-02

Application number

SU772505801A

Other languages

English (en)

Russian (ru)

Inventor

Марк Скотт Ричард

Давид Армитаж Джеффри

Original Assignee

Шелл Интернэшнл Рисерч Маатсхаппийб.B. (Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-08-02

Filing date

1977-08-01

Publication date

1981-04-23

1977-08-01 Application filed by Шелл Интернэшнл Рисерч Маатсхаппийб.B. (Фирма) filed Critical Шелл Интернэшнл Рисерч Маатсхаппийб.B. (Фирма)

1981-04-23 Application granted granted Critical

1981-04-23 Publication of SU824892A3 publication Critical patent/SU824892A3/ru

Links

238000000034 method Methods 0.000 title claims description 6
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
150000002148 esters Chemical class 0.000 claims description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
238000005809 transesterification reaction Methods 0.000 claims description 4
230000003993 interaction Effects 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
239000002585 base Substances 0.000 claims 2
229910001413 alkali metal ion Inorganic materials 0.000 claims 1
150000003863 ammonium salts Chemical class 0.000 claims 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000004009 herbicide Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000047 product Substances 0.000 description 8
238000010533 azeotropic distillation Methods 0.000 description 7
238000009835 boiling Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 description 4
WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
LLJWLIDUVHLMAH-UHFFFAOYSA-N 2-hydroxypropanoic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(O)C(O)=O LLJWLIDUVHLMAH-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
ZMLMOOOPSWVIHJ-SSDOTTSWSA-N ethyl (2r)-2-(2,4-dichlorophenoxy)propanoate Chemical compound CCOC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl ZMLMOOOPSWVIHJ-SSDOTTSWSA-N 0.000 description 2
QOOFWHJIVSELIO-SECBINFHSA-N ethyl (2r)-2-(4-chloro-2-methylphenoxy)propanoate Chemical compound CCOC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C QOOFWHJIVSELIO-SECBINFHSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
ZLSWBLPERHFHIS-SCSAIBSYSA-N (2r)-2-(2,4,5-trichlorophenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-SCSAIBSYSA-N 0.000 description 1
QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical class CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
FBZAJTXIEOKQDV-UHFFFAOYSA-N CC1=C(C=CC=C1)O.[Cl] Chemical compound CC1=C(C=CC=C1)O.[Cl] FBZAJTXIEOKQDV-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
PSFYVNVZQYWSRW-UHFFFAOYSA-N ethanol;tin Chemical compound [Sn].CCO PSFYVNVZQYWSRW-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
230000010287 polarization Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SU772505801A 1976-08-02 1977-08-01 Способ получени производных феноксипропионовойКиСлОТы SU824892A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3208676A GB1586462A (en)	1976-08-02	1976-08-02	Phenonyalkanoic acids and derivatives thereof useful as herbicides

Publications (1)

Publication Number	Publication Date
SU824892A3 true SU824892A3 (ru)	1981-04-23

Family

ID=10333007

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU772505801A SU824892A3 (ru)	1976-08-02	1977-08-01	Способ получени производных феноксипропионовойКиСлОТы

Country Status (11)

Country	Link
JP (1)	JPS5318526A (de)
BE (1)	BE857192A (de)
CA (1)	CA1159468A (de)
CH (1)	CH630883A5 (de)
DD (1)	DD132429A5 (de)
DE (1)	DE2734667A1 (de)
FR (1)	FR2371414A1 (de)
GB (1)	GB1586462A (de)
HU (1)	HU179789B (de)
NL (1)	NL7708416A (de)
SU (1)	SU824892A3 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7129274B1 (en)	1999-11-05	2006-10-31	Emisphere Technologies Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents
US7279597B1 (en)	1999-11-05	2007-10-09	Emisphere Technologies, Inc.	Phenyl amine carboxylic acid compounds and compositions for delivering active agents

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE878446A (fr) *	1978-08-28	1980-02-27	Ppg Industries Inc	Acides trichloro-phenoxy-alcanoiques exempts de dibenzo-p-dioxines chlorees et leur preparation
CA1147348A (en) *	1978-09-19	1983-05-31	Willem Eveleens	Process for the preparation of optically active 2-phenoxy propionic acids and herbicidal preparations containing such acids
JPS579701A (en) *	1980-06-20	1982-01-19	Kumiai Chem Ind Co Ltd	Herbicide containing optically active (+)-2-pentenoic acid compound
DE102007056817A1 (de) *	2007-11-23	2009-05-28	Lanxess Deutschland Gmbh	n-Alkylester der R-(+)-MCPP-Säure
CN106366020B (zh) *	2016-08-31	2018-12-11	京博农化科技股份有限公司	一种合成手性稻瘟酰胺的方法
CN107473962B (zh) *	2017-08-09	2021-12-07	科顺防水科技股份有限公司	一种(r)-2-(4-氯-2-甲基苯氧)丙酸辛酯阻根剂的制备方法
CN108752205B (zh) *	2018-06-28	2021-03-26	科顺防水科技股份有限公司	一种(r)-2-(4-氯-2-甲基苯氧)丙酸辛酯阻根剂的工业化生产改进工艺
CN116554026A (zh) *	2023-05-12	2023-08-08	湖南维摩科技有限公司	一种植物根系抑制剂的合成方法
CN116621697A (zh) *	2023-05-23	2023-08-22	南京工业大学	一种右旋2-（2,4-二氯苯氧基）丙酸的制备方法
CN116789545A (zh) *	2023-05-23	2023-09-22	南京工业大学	一种r-（+）-2-（2,4-二氯苯氧基）丙酸的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1065062B (it) *	1975-08-08	1985-02-25	Hoffmann La Roche	Esteri di acidi alfa arilossicar bossilici sostituiti

1976
- 1976-08-02 GB GB3208676A patent/GB1586462A/en not_active Expired
1977
- 1977-07-13 CA CA000282664A patent/CA1159468A/en not_active Expired
- 1977-07-27 BE BE1008303A patent/BE857192A/xx not_active IP Right Cessation
- 1977-07-29 NL NL7708416A patent/NL7708416A/xx not_active Application Discontinuation
- 1977-07-29 CH CH944577A patent/CH630883A5/de not_active IP Right Cessation
- 1977-08-01 DE DE19772734667 patent/DE2734667A1/de not_active Withdrawn
- 1977-08-01 FR FR7723613A patent/FR2371414A1/fr active Granted
- 1977-08-01 DD DD20037077A patent/DD132429A5/de unknown
- 1977-08-01 JP JP9149477A patent/JPS5318526A/ja active Pending
- 1977-08-01 HU HUSE001866 patent/HU179789B/hu unknown
- 1977-08-01 SU SU772505801A patent/SU824892A3/ru active

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7129274B1 (en)	1999-11-05	2006-10-31	Emisphere Technologies Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents
US7279597B1 (en)	1999-11-05	2007-10-09	Emisphere Technologies, Inc.	Phenyl amine carboxylic acid compounds and compositions for delivering active agents
US7951971B1 (en)	1999-11-05	2011-05-31	Emisphere Technologies, Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents
US8410309B2 (en)	1999-11-05	2013-04-02	Emisphere Technologies, Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents

Also Published As

Publication number	Publication date
HU179789B (en)	1982-12-28
DD132429A5 (de)	1978-09-27
DE2734667A1 (de)	1978-02-09
GB1586462A (en)	1981-03-18
CH630883A5 (en)	1982-07-15
FR2371414B1 (de)	1980-02-01
BE857192A (nl)	1978-01-27
JPS5318526A (en)	1978-02-20
FR2371414A1 (fr)	1978-06-16
CA1159468A (en)	1983-12-27
NL7708416A (nl)	1978-02-06

Publication	Publication Date	Title
SU824892A3 (ru)	1981-04-23	Способ получени производных феноксипропионовойКиСлОТы
DK152726B (da)	1988-05-02	Fremgangsmaade til fremstilling af monoacetaler af aromatiske 1,2-diketoner
EP0081993B1 (de)	1988-08-17	Optisch aktive alpha-substituierte Arylketone, Verfahren zu ihrer Herstellung und ihre Anwendung in der Herstellung von alpha-Arylalkancarbonsäuren
US3651106A (en)	1972-03-21	Preparation of 2-(6-methoxy-2-naphthyl)propionic acid -1-propanol and propanal and intermediates therefor
SU764608A3 (ru)	1980-09-15	Способ получени фторированных производных алкановых кислот или их солей или их оптически активных изомеров
JP2007269657A (ja)	2007-10-18	α−グリセロホスホリルコリン結晶の製造方法
Royals	1945	The use of sodium methoxide in the Claisen reaction
RU2174514C2 (ru)	2001-10-10	Способы получения производных феноксипропионовой кислоты (варианты)
CN113135887A (zh)	2021-07-20	一种碳酸多元醇酯的制备方法
SU639443A3 (ru)	1978-12-25	Способ получени производных 3-амино-2-оксипропана или их солей
SU520038A3 (ru)	1976-06-30	Способ получени (1-бис-аралкил-аминоалкил)аралкоксибензиловых спиртов или их солей, рацематов или оптически-активных антиподов
US3906038A (en)	1975-09-16	2-(6-Sulfo-2-naphthyl)propionic acid
EP0154853B1 (de)	1988-01-20	Verfahren zur Herstellung von optisch aktiven alpha-Arylalkansäuren
JPH082821B2 (ja)	1996-01-17	１，４，５，８−テトラキス（ヒドロキシメチル）ナフタレン誘導体およびその製造方法
SU493961A3 (ru)	1975-11-28	Способ получени производных 6 метилпреднизолона
US4965398A (en)	1990-10-23	Process for producing optically active alpha-hydroxycarboxylates
EP0138521B1 (de)	1989-03-22	Verfahren zur Herstellung von d-alpha-(6-Methoxy-2-naphthyl)-Propionsäure
SU1209025A3 (ru)	1986-01-30	Способ получени @ -феноксибензилового спирта
US2669574A (en)	1954-02-16	Esters of organic sulfonic acids
US2867650A (en)	1959-01-06	Process for the preparation of monodiol esters of terephthalic acid
US2770647A (en)	1956-11-13	Quaternary ammonium compounds of basic esters of 2-aryl-2-(1-hydroxycyclopentyl) ethanoic acids
US2129317A (en)	1938-09-06	Process for the manufacture of laevoascorbic acid
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