CA1338512C - Acide 2-(4-acetoxyphenoxy)propanoique - Google Patents

Acide 2-(4-acetoxyphenoxy)propanoique

Info

Publication number: CA1338512C
Authority: CA; Canada
Prior art keywords: acid; reaction; propanoic acid; acids; acetoxyphenoxy
Prior art date: 1988-03-21
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.): Expired - Fee Related

Application number

CA000616943A

Other languages

English (en)

Inventor

Varadaraj Elango

Kenneth G. Davenport

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

CNA Holdings LLC

Original Assignee

Hoechst Celanese Corp

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.)

1988-03-21

Filing date

1994-11-04

Publication date

1996-08-06

1988-03-21 Priority claimed from US07/170,728 external-priority patent/US4908476A/en

1994-11-04 Application filed by Hoechst Celanese Corp filed Critical Hoechst Celanese Corp

1996-08-06 Application granted granted Critical

1996-08-06 Publication of CA1338512C publication Critical patent/CA1338512C/fr

2009-03-15 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

APDIEUFOBVDFBQ-UHFFFAOYSA-N 2-(4-acetyloxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(OC(C)=O)C=C1 APDIEUFOBVDFBQ-UHFFFAOYSA-N 0.000 title claims abstract description 6
239000002253 acid Substances 0.000 abstract description 31
150000007513 acids Chemical class 0.000 abstract description 12
238000004519 manufacturing process Methods 0.000 abstract description 5
230000015572 biosynthetic process Effects 0.000 abstract description 4
239000004009 herbicide Substances 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
239000000975 dye Substances 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 20
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 16
238000000034 method Methods 0.000 description 14
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 10
238000010992 reflux Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 9
-1 4-acetoxyphenoxy Chemical group 0.000 description 8
229940073735 4-hydroxy acetophenone Drugs 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LMBHCEXLVUOTAV-UHFFFAOYSA-N 2-(4-acetylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(C(C)=O)C=C1 LMBHCEXLVUOTAV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000006136 alcoholysis reaction Methods 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 description 3
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 3
238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
238000003797 solvolysis reaction Methods 0.000 description 3
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
ZHMMPVANGNPCBW-UHFFFAOYSA-N 4-Hydroxyhydratropate Chemical group OC(=O)C(C)C1=CC=C(O)C=C1 ZHMMPVANGNPCBW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000009833 condensation Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002243 precursor Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
JSQPGNJFQUOEPA-UHFFFAOYSA-N 2-chloroethaneperoxoic acid Chemical compound OOC(=O)CCl JSQPGNJFQUOEPA-UHFFFAOYSA-N 0.000 description 1
GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
HLKQRSOYMIVDEV-UHFFFAOYSA-N ethyl 2-(2-methylphenyl)sulfonyloxypropanoate Chemical compound CCOC(=O)C(C)OS(=O)(=O)C1=CC=CC=C1C HLKQRSOYMIVDEV-UHFFFAOYSA-N 0.000 description 1
JEAVBVKAYUCPAQ-UHFFFAOYSA-N ethyl 2-chloropropanoate Chemical compound CCOC(=O)C(C)Cl JEAVBVKAYUCPAQ-UHFFFAOYSA-N 0.000 description 1
LONGCUIECIAYIP-UHFFFAOYSA-N ethyl 2-methylsulfonyloxypropanoate Chemical compound CCOC(=O)C(C)OS(C)(=O)=O LONGCUIECIAYIP-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
102200073741 rs121909602 Human genes 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000616943A 1988-03-21 1994-11-04 Acide 2-(4-acetoxyphenoxy)propanoique Expired - Fee Related CA1338512C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/170,728 US4908476A (en)	1988-03-21	1988-03-21	Synthesis of 2-(4-hydroxyphenoxy)alkanoic acids
US170,728		1988-03-21
CA000593713A CA1335598C (fr)	1988-03-21	1989-03-15	Synthese d'acides 2-(4-hydroxyphenoxy)alcanoiques

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000593713A Division CA1335598C (fr)	1988-03-21	1989-03-15	Synthese d'acides 2-(4-hydroxyphenoxy)alcanoiques

Publications (1)

Publication Number	Publication Date
CA1338512C true CA1338512C (fr)	1996-08-06

Family

ID=25672524

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616943A Expired - Fee Related CA1338512C (fr)	1988-03-21	1994-11-04	Acide 2-(4-acetoxyphenoxy)propanoique

Country Status (1)

Country	Link
CA (1)	CA1338512C (fr)

1994
- 1994-11-04 CA CA000616943A patent/CA1338512C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2000-08-07	MKLA	Lapsed

Publication	Publication Date	Title
US4908476A (en)	1990-03-13	Synthesis of 2-(4-hydroxyphenoxy)alkanoic acids
CA1338512C (fr)	1996-08-06	Acide 2-(4-acetoxyphenoxy)propanoique
JPH03372B2 (fr)	1991-01-07
JP3929545B2 (ja)	2007-06-13	３−アセチル−シクロペンタンカルボン酸エステルの製造方法
US5008439A (en)	1991-04-16	Synthesis of 2-(4-hydroxyphenoxy) alkanoic acid esters
US4883901A (en)	1989-11-28	Synthesis of 2-(4-aminophenoxy)alkanoic acids and esters and their derivatives
US4935522A (en)	1990-06-19	Process for producing ethyl 2-[4'-(6"-chloro-2"-benzoxazolyloxy)phenoxy]propionate
KR0149499B1 (ko)	1998-10-15	삼중치환 벤조산 중간체
US4393008A (en)	1983-07-12	2-Cyano-2-(3-phenoxy-phenyl)-propionic acid amide and preparation thereof
JPH0696545B2 (ja)	1994-11-30	３，５，６−トリフルオロ−４−ヒドロキシフタル酸の製造法
US5329041A (en)	1994-07-12	Trisubstituted benzoic acid intermediates
JPH02223542A (ja)	1990-09-05	ヒドロアトロパ酸誘導体およびそのエステルの製造方法
US5235090A (en)	1993-08-10	Synthesis of 2-(4'-aminophenyloxy) alkanoic acids & acids & esters & their derivatives
CN112694403A (zh)	2021-04-23	一种制备(r)-(+)-2-(4-羟基苯氧基)丙酸甲酯的方法
KR100635115B1 (ko)	2006-10-18	알파-아릴알칸산의 제조방법
JPH0611736B2 (ja)	1994-02-16	光学活性なα−（４−ヒドロキシフエノキシ）プロピオン酸エステルの製法
EP1007501A1 (fr)	2000-06-14	Procede de production de diphenylethers et d'esters
JP3830749B2 (ja)	2006-10-11	光学活性４，４，４−トリフルオロ−３−ヒドロキシブタン酸アリールエステル誘導体の製造方法
CS221849B2 (en)	1983-04-29	Method of making the m-phenoxybenzylalcohol and derivatives thereof
KR930011037B1 (ko)	1993-11-20	퀴놀린 카르본산 유도체의 제조방법
KR100290535B1 (ko)	2001-09-17	2-페닐알칸산의제조방법
JPH0414093B2 (fr)	1992-03-11
KR920006783B1 (ko)	1992-08-17	항혈액응고성 살서제인 4-하이드록시쿠마린 유도체의 제조방법
CA2412267A1 (fr)	2002-01-10	Procede pour la production d'aldehydes aliphatiques, aromatiques ou heteroaromatiques eventuellement substitues
JPH0665245A (ja)	1994-03-08	ピリジン−２，３−ジカルボン酸無水物の製造法