GB1270413A - ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDS - Google Patents
ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDSInfo
- Publication number
- GB1270413A GB1270413A GB9653/70A GB965370A GB1270413A GB 1270413 A GB1270413 A GB 1270413A GB 9653/70 A GB9653/70 A GB 9653/70A GB 965370 A GB965370 A GB 965370A GB 1270413 A GB1270413 A GB 1270413A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclopropylmethoxy
- group
- pyrocatechol
- esters
- alkylidene
- 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.)
- Expired
Links
- 150000002691 malonic acids Chemical class 0.000 title abstract 2
- -1 alkylidene malonic acid esters Chemical class 0.000 abstract 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- YPYVHBAOWPFXEZ-UHFFFAOYSA-N (2-decoxy-5-nitrophenyl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=CC(=C1)[N+](=O)[O-])OCCCCCCCCCC YPYVHBAOWPFXEZ-UHFFFAOYSA-N 0.000 abstract 1
- WZFSJNLQOGQSTH-UHFFFAOYSA-N (2-decoxyphenyl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=CC=C1)OCCCCCCCCCC WZFSJNLQOGQSTH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract 1
- NDRKSQOMYVDSGD-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-2-decoxy-4-nitrobenzene Chemical compound C(CCCCCCCCC)OC=1C=C(C=CC1OCC1CC1)[N+](=O)[O-] NDRKSQOMYVDSGD-UHFFFAOYSA-N 0.000 abstract 1
- GMBSDHNFVJXBSD-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-2-dodecoxy-4-nitrobenzene Chemical compound C(CCCCCCCCCCC)OC=1C=C(C=CC1OCC1CC1)[N+](=O)[O-] GMBSDHNFVJXBSD-UHFFFAOYSA-N 0.000 abstract 1
- PEDVRNCAYQZEQC-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-4-nitro-2-octoxybenzene Chemical compound C(CCCCCCC)OC=1C=C(C=CC1OCC1CC1)[N+](=O)[O-] PEDVRNCAYQZEQC-UHFFFAOYSA-N 0.000 abstract 1
- IZJAXMGHAFLFMH-UHFFFAOYSA-N 2-(anilinomethylidene)propanedioic acid Chemical compound OC(=O)C(C(O)=O)=CNC1=CC=CC=C1 IZJAXMGHAFLFMH-UHFFFAOYSA-N 0.000 abstract 1
- SRXNQUQBVGGLAX-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-1-decoxy-3-nitrobenzene Chemical compound C1(CC1)COC1=C(C=CC=C1OCCCCCCCCCC)[N+](=O)[O-] SRXNQUQBVGGLAX-UHFFFAOYSA-N 0.000 abstract 1
- ADDQNDLHSCOIBM-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-1-decoxy-4-nitrobenzene Chemical compound C1(CC1)COC=1C=C(C=CC1OCCCCCCCCCC)[N+](=O)[O-] ADDQNDLHSCOIBM-UHFFFAOYSA-N 0.000 abstract 1
- YDZSEXUMNNEHKE-UHFFFAOYSA-N 2-(cyclopropylmethoxy)phenol Chemical compound OC1=CC=CC=C1OCC1CC1 YDZSEXUMNNEHKE-UHFFFAOYSA-N 0.000 abstract 1
- BMTZYZNEISFFOM-UHFFFAOYSA-N 2-[2-(cyclopropylmethoxy)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1OCC1CC1 BMTZYZNEISFFOM-UHFFFAOYSA-N 0.000 abstract 1
- BQWZWEJXJVHFSI-UHFFFAOYSA-N 2-decoxy-5-nitrophenol Chemical compound CCCCCCCCCCOC1=CC=C([N+]([O-])=O)C=C1O BQWZWEJXJVHFSI-UHFFFAOYSA-N 0.000 abstract 1
- NOJIVXPLDDHVSU-UHFFFAOYSA-N 2-decoxyphenol Chemical compound CCCCCCCCCCOC1=CC=CC=C1O NOJIVXPLDDHVSU-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- GVFCBIBCNWGQDN-UHFFFAOYSA-N [2-(cyclopropylmethoxy)-5-nitrophenyl] benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=CC(=C1)[N+](=O)[O-])OCC1CC1 GVFCBIBCNWGQDN-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- 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
- C07C45/008—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with tri- or tetrahalomethyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Physical Water Treatments (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Quinoline Compounds (AREA)
Abstract
1,270,413. Esters of α-(1-phenylamino-1,1- alkylidene) malonic acids. CIBA-GEIGY A.G. 16 June, 1969 [14 June, 1968; 24 Oct., 1968; 18 March, 1969], No. 9653/70. Divided out of 1,270,412. Addition to 1,205,639. Heading C2C. Novel alkylidene malonic acid esters of the formula in which Ph is a 1,2-phenylene residue substituted by a group -X 1 -A-R<SP>I</SP> and a group -X 2 -R<SP>II</SP> (in which RI is a cycloaliphatic radical, A is a direct bond or a bivalent aliphatic radical, each of X 1 and X 2 is oxygen or sulphur and R<SP>II</SP> is a C 8-20 aliphatic group), each of R 0 and R<SP>0</SP> 1 is carbo-C 1-7 -alkoxy, R 2 is hydrogen or C 1-7 alkyl and R 3 is hydrogen or an optionally substituted aliphatic or cycloaliphatic radical, or the tautomer of such a compound in which R 3 is hydrogen, are prepared by condensing an aniline containing the appropriate -X 1 -A-R<SP>I</SP> or -X 2 -R<SP>II</SP> substituents with a di-C 1-7 alkyl ester of an α-(1-C 1-7 alkoxy-1,1-alkylidene) malonic acid. Preferred compounds are dimethyl and diethyl esters of phenylaminomethylene-malonic acid in which the phenyl group is substituted by a cyclopropylmethoxy group and a decyloxy, dodecyloxy, octyloxy or tetradecyloxy group. The substituted aniline reactants are obtained by reduction of the co-responding nitro compounds. 4-Cyclopropylmethoxy - 3 - decyloxynitrobenzene is obtained by reacting cyclopropylmethyl bromide with pyrocatechol to yield pyrocatechol monocyclopropylmethyl ether which is condensed with benzoyl chloride to obtain 2- cyclopropylmethoxy-phenylbenzoate which is nitrated to 2 - cyclopropylmethoxy - 5 - nitrophenyl benzoate which on hydrolysis yields 4- ayclopropylmethoxy - 3 - hydroxy - nitrobenzene, reaction with decyl bromide providing the required ether. 3 - Cyclopropylmethoxy - 4- decyloxynitrobenzene is obtained by reacting pyrocatechol with decyl bromide, esterifying the resultant pyrocatechol monodecyl ether with benzoyl chloride to obtain 2-decyloxyphenyl benzoate which is nitrated, hydrolysing the 2- decyloxy - 5 - nitrophenyl benzoate obtained to 4 - decyloxy - 3 - hydroxy - nitrobenzene and reacting this with cyclopropylmethyl bromide to obtain the diether. 4-Cyclopropylmethoxy-3- dodecyloxy - nitrobenzene, 4 - cyclopropylmethoxy - 3 - octyloxynitrobenzene, and 2 - cyclopropylmethoxy-3-decyloxynitrobenzene are prepared by similar methods.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73696268A | 1968-06-14 | 1968-06-14 | |
| US77042668A | 1968-10-24 | 1968-10-24 | |
| US80833369A | 1969-03-18 | 1969-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1270413A true GB1270413A (en) | 1972-04-12 |
Family
ID=27419219
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9653/70A Expired GB1270413A (en) | 1968-06-14 | 1969-06-16 | ESTERS OF alpha-1-AMINO-1,1-ALKYLIDENE MALONIC ACIDS |
| GB30403/69A Expired GB1270412A (en) | 1968-06-14 | 1969-06-16 | 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30403/69A Expired GB1270412A (en) | 1968-06-14 | 1969-06-16 | 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS504673B1 (en) |
| AT (2) | AT319725B (en) |
| BE (1) | BE734566A (en) |
| CH (2) | CH560193A5 (en) |
| DE (1) | DE1929165A1 (en) |
| ES (1) | ES368288A2 (en) |
| FI (1) | FI49407C (en) |
| FR (1) | FR2010879B1 (en) |
| GB (2) | GB1270413A (en) |
| IE (1) | IE33810B1 (en) |
| IL (1) | IL32362A0 (en) |
| KE (2) | KE2548A (en) |
| MY (2) | MY7500154A (en) |
| NL (1) | NL6908370A (en) |
| NO (2) | NO132868C (en) |
| RO (1) | RO56838A (en) |
| SE (2) | SE387223B (en) |
| SU (1) | SU561492A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0262305A1 (en) * | 1986-08-29 | 1988-04-06 | American Cyanamid Company | Method for the preparation of anilinofumarate and quinoline-2,3-dicarboxylic acid |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU997646A1 (en) * | 1978-11-27 | 1983-02-23 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвсср | Fodder additive |
| JPS58219166A (en) * | 1982-06-14 | 1983-12-20 | Nippon Shinyaku Co Ltd | 4-quinolone derivative |
| IL159320A0 (en) | 2001-06-12 | 2004-06-01 | Wellstat Therapeutics Corp | Compounds for the treatment of metabolic disorders |
| AR099860A1 (en) * | 2014-03-26 | 2016-08-24 | Procter & Gamble | PERFUME SYSTEMS |
-
1969
- 1969-05-12 CH CH724969A patent/CH560193A5/xx not_active IP Right Cessation
- 1969-06-02 NL NL6908370A patent/NL6908370A/xx not_active Application Discontinuation
- 1969-06-08 IL IL32362A patent/IL32362A0/en unknown
- 1969-06-09 DE DE19691929165 patent/DE1929165A1/en active Pending
- 1969-06-10 FR FR6919073A patent/FR2010879B1/fr not_active Expired
- 1969-06-11 IE IE800/69A patent/IE33810B1/en unknown
- 1969-06-11 SE SE7206919A patent/SE387223B/en unknown
- 1969-06-11 SE SE08293/69A patent/SE362424B/xx unknown
- 1969-06-12 ES ES368288A patent/ES368288A2/en not_active Expired
- 1969-06-13 FI FI691755A patent/FI49407C/en active
- 1969-06-13 NO NO2456/69A patent/NO132868C/no unknown
- 1969-06-13 AT AT01300/71A patent/AT319725B/en not_active IP Right Cessation
- 1969-06-13 JP JP44046446A patent/JPS504673B1/ja active Pending
- 1969-06-13 BE BE734566D patent/BE734566A/xx unknown
- 1969-06-13 AT AT563069A patent/AT301547B/en not_active IP Right Cessation
- 1969-06-14 RO RO60235A patent/RO56838A/ro unknown
- 1969-06-16 GB GB9653/70A patent/GB1270413A/en not_active Expired
- 1969-06-16 GB GB30403/69A patent/GB1270412A/en not_active Expired
-
1970
- 1970-10-22 SU SU1488051A patent/SU561492A3/en active
-
1973
- 1973-03-16 NO NO1068/73A patent/NO137072C/en unknown
-
1974
- 1974-06-20 CH CH846174A patent/CH610732A5/en not_active IP Right Cessation
-
1975
- 1975-07-16 KE KE2548*UA patent/KE2548A/en unknown
- 1975-07-16 KE KE2547*UA patent/KE2547A/en unknown
- 1975-12-30 MY MY154/75A patent/MY7500154A/en unknown
- 1975-12-30 MY MY153/75A patent/MY7500153A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0262305A1 (en) * | 1986-08-29 | 1988-04-06 | American Cyanamid Company | Method for the preparation of anilinofumarate and quinoline-2,3-dicarboxylic acid |
| AU598023B2 (en) * | 1986-08-29 | 1990-06-14 | American Cyanamid Company | Novel method for the preparation of quinoline-2, 3-dicarboxylic acid with anilinefumarates and dialkyloxalacetates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2010879A1 (en) | 1970-02-20 |
| KE2547A (en) | 1975-08-01 |
| JPS504673B1 (en) | 1975-02-22 |
| AT319725B (en) | 1975-01-10 |
| MY7500154A (en) | 1975-12-31 |
| IE33810B1 (en) | 1974-11-13 |
| SE387223B (en) | 1976-09-06 |
| NL6908370A (en) | 1969-12-16 |
| GB1270412A (en) | 1972-04-12 |
| FI49407C (en) | 1975-06-10 |
| AT301547B (en) | 1972-09-11 |
| NO137072C (en) | 1977-12-28 |
| NO132868B (en) | 1975-10-13 |
| NO132868C (en) | 1976-01-21 |
| IE33810L (en) | 1969-12-14 |
| CH610732A5 (en) | 1979-05-15 |
| IL32362A0 (en) | 1969-08-27 |
| SE362424B (en) | 1973-12-10 |
| KE2548A (en) | 1975-08-01 |
| RO56838A (en) | 1975-03-15 |
| SU561492A3 (en) | 1977-06-05 |
| NO137072B (en) | 1977-09-19 |
| FR2010879B1 (en) | 1976-09-03 |
| DE1929165A1 (en) | 1969-12-18 |
| BE734566A (en) | 1969-12-15 |
| MY7500153A (en) | 1975-12-31 |
| FI49407B (en) | 1975-02-28 |
| CH560193A5 (en) | 1975-03-27 |
| ES368288A2 (en) | 1971-05-01 |
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