JP7065119B2 - ペンテノエートの調製プロセス - Google Patents
ペンテノエートの調製プロセス Download PDFInfo
- Publication number
- JP7065119B2 JP7065119B2 JP2019565054A JP2019565054A JP7065119B2 JP 7065119 B2 JP7065119 B2 JP 7065119B2 JP 2019565054 A JP2019565054 A JP 2019565054A JP 2019565054 A JP2019565054 A JP 2019565054A JP 7065119 B2 JP7065119 B2 JP 7065119B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound represented
- weight
- acid
- present
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
で表される化合物を調製するためのプロセスであって、以下の:、
a)以下の式(2):
b)その後、式(4)で表される化合物を酸と接触させて、式(1)で表される化合物を得るステップと、を含み、
ステップ(a)及び/又はステップ(b)が、連続モ-ドで行われる、プロセスに関する。
(d)以下の式(6):
で表される化合物を調製するためのプロセスであって、
(a)以下の式(5):
で表される化合物を調製するためのプロセスであって、
(a)以下の式(6)の化合物:
連続撹拌タンク反応器に、14gのグリセロ-ル、40gのKHSO4、及び8gのK2SO4を入れる。混合物を200~230℃まで加熱する。次いで、連続動作中に、グリセロ-ルを90分かけて380μL/分の速度で添加する。グリセロ-ルの添加中、アクロレイン及び水を390μl/分の一定速度で留去するため撹拌タンク反応器内の容積を1mlで一定に保つ必要がある。90分の間に35.1mlが蒸留された。留出物は、水及びアクロレインで構成されていた。
連続撹拌タンク反応器に、28gのグリセロ-ル、80gのKHSO4、及び16gのK2SO4を入れる。混合物を200~230℃まで加熱する。次いで、連続動作中に、グリセロ-ルを300分かけて1600μL/分の速度で添加する。グリセロ-ルの添加中、アクロレイン及び水は、1230μl/分の一定速度で留去された。300分の間に365mlが蒸留された。留出物は、水及びアクロレインで構成されていた。
図1に描写された配置では、示された組成物の示されたプロセスフロ-が反応して、82%の粗収率(tert-ブチルアセテ-トに基づく)及び86%の純度(1H-NMR、内部標準としてピリジンにより決定)で、71%の純粋な生成物の収率を示す、R1=tert.ブチル及びR2=R3=R4=Hである化合物(1)を形成する。
Claims (5)
- 以下の式(1):
で表される化合物を調製するためのプロセスであって、以下の:、
a)以下の式(2):
で表される化合物を、
以下の式(3):
で表される化合物と接触させて、以下の式(4):
b)その後、前記式(4)で表される化合物を酸と接触させて、前記式(1)で表される化合物を得るステップと、を含み、ここで、ステップ(a)は、少なくとも0℃で行われ、かつ、
ステップ(a)及び/又はステップ(b)は、連続モ-ドで行われる、プロセス。 - ステップ(c)は、連続モ-ドで行われる、請求項2に記載のプロセス。
- ステップ(d)は、連続モードで行われる、請求項4に記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP17155927.1 | 2017-02-13 | ||
EP17155927.1A EP3360857A1 (en) | 2017-02-13 | 2017-02-13 | Process for preparing pentenoate |
PCT/EP2018/053434 WO2018146306A1 (en) | 2017-02-13 | 2018-02-12 | Process for preparing pentenoate |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020508346A JP2020508346A (ja) | 2020-03-19 |
JP7065119B2 true JP7065119B2 (ja) | 2022-05-11 |
Family
ID=58043928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019565054A Active JP7065119B2 (ja) | 2017-02-13 | 2018-02-12 | ペンテノエートの調製プロセス |
Country Status (8)
Country | Link |
---|---|
US (1) | US10843999B2 (ja) |
EP (2) | EP3360857A1 (ja) |
JP (1) | JP7065119B2 (ja) |
CN (1) | CN110573488B (ja) |
ES (1) | ES2965241T3 (ja) |
IL (1) | IL268566B (ja) |
TW (1) | TWI799408B (ja) |
WO (1) | WO2018146306A1 (ja) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005103280A1 (ja) | 2004-04-21 | 2005-11-03 | Toyo Kasei Kogyo Co., Ltd. | 光学活性な4-(n-保護アミノ)-1-アルケン-3-オールの製造方法、およびそれを用いた3-ベンザミド-2-ヒドロキシカルボン酸またはその塩の製造方法 |
US20130267719A1 (en) | 2010-08-19 | 2013-10-10 | Peter Mikochik | Conversion of 5-(chloromethyl)-2-furaldehyde into 5-methyl-2-furoic acid and derivatives thereof |
JP2013545732A (ja) | 2010-10-26 | 2013-12-26 | アディッソ・フランス・エス.エー.エス. | グリセロールまたはグリセリンの接触脱水によりアクロレインを得るための方法 |
US20140051869A1 (en) | 2009-10-23 | 2014-02-20 | Phoenix Chemicals Limited | Continuous process for the production of beta-keto esters by claisen condensation |
US20150087861A1 (en) | 2012-04-18 | 2015-03-26 | Arkema France | Method for producing acrolein and/or acrylic acid from glycerol |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1148155A (en) * | 1980-01-21 | 1983-06-14 | Alexander F. Orr | Tetrahydrofuran derivatives, a process for their preparation, herbicidal compositions containing them and a method of controlling undesired plant growth using them |
JP5304299B2 (ja) * | 2009-02-12 | 2013-10-02 | 株式会社日立プラントテクノロジー | 臨界水を用いた反応プロセス |
US9273257B2 (en) * | 2009-06-05 | 2016-03-01 | Tara C. Mancini | Process for continuous production of biodiesel from fatty acid containing feedstocks |
CN104529842A (zh) * | 2014-12-22 | 2015-04-22 | 泰州施美康多肽药物技术有限公司 | 一种缩酯环肽类组蛋白去乙酰化酶抑制剂的中间体及其制备方法 |
-
2017
- 2017-02-13 EP EP17155927.1A patent/EP3360857A1/en not_active Ceased
-
2018
- 2018-02-12 ES ES18703605T patent/ES2965241T3/es active Active
- 2018-02-12 CN CN201880013763.6A patent/CN110573488B/zh active Active
- 2018-02-12 US US16/484,364 patent/US10843999B2/en active Active
- 2018-02-12 JP JP2019565054A patent/JP7065119B2/ja active Active
- 2018-02-12 EP EP18703605.8A patent/EP3580196B1/en active Active
- 2018-02-12 WO PCT/EP2018/053434 patent/WO2018146306A1/en active Application Filing
- 2018-02-13 TW TW107105373A patent/TWI799408B/zh active
-
2019
- 2019-08-07 IL IL268566A patent/IL268566B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005103280A1 (ja) | 2004-04-21 | 2005-11-03 | Toyo Kasei Kogyo Co., Ltd. | 光学活性な4-(n-保護アミノ)-1-アルケン-3-オールの製造方法、およびそれを用いた3-ベンザミド-2-ヒドロキシカルボン酸またはその塩の製造方法 |
US20140051869A1 (en) | 2009-10-23 | 2014-02-20 | Phoenix Chemicals Limited | Continuous process for the production of beta-keto esters by claisen condensation |
US20130267719A1 (en) | 2010-08-19 | 2013-10-10 | Peter Mikochik | Conversion of 5-(chloromethyl)-2-furaldehyde into 5-methyl-2-furoic acid and derivatives thereof |
JP2013545732A (ja) | 2010-10-26 | 2013-12-26 | アディッソ・フランス・エス.エー.エス. | グリセロールまたはグリセリンの接触脱水によりアクロレインを得るための方法 |
US20150087861A1 (en) | 2012-04-18 | 2015-03-26 | Arkema France | Method for producing acrolein and/or acrylic acid from glycerol |
Non-Patent Citations (2)
Title |
---|
J. Org. Chem.,1989年,54,4717-4719 |
Org. Lett. ,2015年,17,1353-1356 |
Also Published As
Publication number | Publication date |
---|---|
IL268566A (en) | 2019-09-26 |
EP3580196C0 (en) | 2023-10-25 |
CN110573488B (zh) | 2022-11-04 |
ES2965241T3 (es) | 2024-04-11 |
JP2020508346A (ja) | 2020-03-19 |
TW201840519A (zh) | 2018-11-16 |
WO2018146306A1 (en) | 2018-08-16 |
US10843999B2 (en) | 2020-11-24 |
TWI799408B (zh) | 2023-04-21 |
IL268566B (en) | 2021-10-31 |
EP3580196B1 (en) | 2023-10-25 |
EP3580196A1 (en) | 2019-12-18 |
US20200002263A1 (en) | 2020-01-02 |
CN110573488A (zh) | 2019-12-13 |
EP3360857A1 (en) | 2018-08-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Konik et al. | Two-step conversion of carboxylic esters into distally fluorinated ketones via ring cleavage of cyclopropanol intermediates: application of sulfinate salts as fluoroalkylating reagents | |
Rafiee et al. | Cs2. 5H0. 5PW12O40 catalyzed diastereoselective synthesis of β-amino ketones via three component Mannich-type reaction in water | |
Yanai et al. | A regioselective synthesis of poly-substituted aryl triflones through self-promoting three component reaction | |
Kothandaraman et al. | Gold-and silver-catalyzed allylic alkylation of 1, 3-dicarbonyl compounds with allylic alcohols | |
Carter et al. | The continuous flow synthesis of butane-2, 3-diacetal protected building blocks using microreactors | |
JP5070936B2 (ja) | 2−ヒドロキシ−4−(メチルチオ)酪酸またはそのエステルの製造方法およびその中間体 | |
von Keutz et al. | Continuous flow multistep synthesis of α-functionalized esters via lithium enolate intermediates | |
JP7065119B2 (ja) | ペンテノエートの調製プロセス | |
Guillot et al. | Solvent-free condensation of arylacetonitrile with aldehydes | |
Mashima et al. | Structures of Mono-and Bis (2-butenyl) zirconium complexes in solution and threo selective insertion reaction of aliphatic aldehydes | |
JP2009114135A (ja) | 不斉触媒アルドール反応生成物の製造方法 | |
FR2804427A1 (fr) | Procede de preparation de cetones alpha-halogenees | |
JP4119371B2 (ja) | ルイス酸触媒含有組成物 | |
Ramanjaneyulu et al. | Direct Esterification of Aromatic Aldehydes with Tetraphenylphosphonium Bromide under Oxidative N‐Heterocyclic Carbene Catalysis | |
TW201808871A (zh) | 縮醛化合物之製造方法 | |
EP3848359B1 (en) | Method for producing trifluoropyruvate fluoride dimer, and method for producing perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) | |
JP7223445B2 (ja) | 脱離基を有する有機化合物と有機ケイ素化合物とのカップリング体の製造方法 | |
JP4243683B2 (ja) | 1−テトラロン類の製造方法 | |
Hu et al. | Efficient and convenient oxidation of alcohols to aldehydes and ketones with H 2 O 2/(NH 4) 6 Mo 7 O 24· 4H 2 O regulated by PEG 1000-DIL/methylcyclohexane temperature-dependent biphasic system | |
CN117916223A (zh) | 含有四氟硫基的芳基化合物的制造方法 | |
Sugimoto et al. | Synthesis of 1, 4, 2-dioxazolidines by the reaction of keto aldehydes with N-phenylhydroxylamine. Intramolecular [3+ 2] cycloaddition between the nitrone and carbonyl moieties | |
JPH0142951B2 (ja) | ||
JP2012056852A (ja) | マイクロ空間反応場を利用したクライゼン転位化合物の製造方法及びその装置 | |
BR112020009410B1 (pt) | Método para a preparação de um dialquil ou diaquenil éter de um diol cicloalifático ou aralifático | |
EP3848359A1 (en) | Aldehyde adduct to hexafluoropropylene oxide, method for producing trifluoropyruvate fluoride dimer, and method for producing perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20201111 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20210812 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210914 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20211213 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20220412 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220425 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7065119 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |