DD232484A5 - Verfahren zur herstellung von monoethern von dihydroxylbenzolen - Google Patents

Verfahren zur herstellung von monoethern von dihydroxylbenzolen Download PDF

Info

Publication number: DD232484A5
Authority: DD; German Democratic Republic
Prior art keywords: methylethenyl; phenoxy; methyl; propanoate; item
Prior art date: 1983-06-24

Application number

DD84264435A

Other languages

German (de)

English (en)

Inventor

Abel Mendoza

Eric W Otterbacher

Original Assignee

Dow Chemical Co

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.)

1983-06-24

Filing date

1984-06-22

Publication date

1986-01-29

1984-06-22 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1986-01-29 Publication of DD232484A5 publication Critical patent/DD232484A5/de

Links

238000000034 method Methods 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title description 3
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title 1
238000002360 preparation method Methods 0.000 claims abstract description 27
239000002168 alkylating agent Substances 0.000 claims abstract description 12
229940100198 alkylating agent Drugs 0.000 claims abstract description 12
150000005205 dihydroxybenzenes Chemical class 0.000 claims abstract description 6
239000003377 acid catalyst Substances 0.000 claims abstract description 3
230000001590 oxidative effect Effects 0.000 claims abstract 2
-1 2-ethoxyethyl ester Chemical class 0.000 claims description 26
150000002148 esters Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 6
WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 claims description 4
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
GFIXNOPYGBPRFH-UHFFFAOYSA-N 2-(4-prop-1-en-2-ylphenoxy)acetonitrile Chemical compound CC(=C)C1=CC=C(OCC#N)C=C1 GFIXNOPYGBPRFH-UHFFFAOYSA-N 0.000 claims description 3
WPFRITDHEFXFCX-UHFFFAOYSA-N 2-(4-prop-1-en-2-ylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(C(C)=C)C=C1 WPFRITDHEFXFCX-UHFFFAOYSA-N 0.000 claims description 3
QJFBFFPAVLVAHO-UHFFFAOYSA-N 2-ethoxyethyl 2-(4-prop-1-en-2-ylphenoxy)propanoate Chemical compound CCOCCOC(=O)C(C)OC1=CC=C(C(C)=C)C=C1 QJFBFFPAVLVAHO-UHFFFAOYSA-N 0.000 claims description 3
GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical group CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
229940106681 chloroacetic acid Drugs 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
WQDYHSNCMYSEIS-UHFFFAOYSA-N methyl 2-(4-prop-1-en-2-ylphenoxy)propanoate Chemical compound COC(=O)C(C)OC1=CC=C(C(C)=C)C=C1 WQDYHSNCMYSEIS-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
230000029936 alkylation Effects 0.000 description 8
238000005804 alkylation reaction Methods 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
UUYSCNGPNOYZMC-UHFFFAOYSA-N methyl 2-(4-hydroxyphenoxy)propanoate Chemical compound COC(=O)C(C)OC1=CC=C(O)C=C1 UUYSCNGPNOYZMC-UHFFFAOYSA-N 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
OITXOTZGDJLEBU-UHFFFAOYSA-N methyl 2-(4-hydroxyphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(O)C=C1 OITXOTZGDJLEBU-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
125000006018 1-methyl-ethenyl group Chemical group 0.000 description 3
KDTJYHQWVKLPNI-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)acetonitrile Chemical compound OC1=CC=C(OCC#N)C=C1 KDTJYHQWVKLPNI-UHFFFAOYSA-N 0.000 description 3
HQMCVCIGYWWYPC-UHFFFAOYSA-N 2-(4-prop-1-en-2-ylphenoxy)ethanol Chemical compound CC(=C)C1=CC=C(OCCO)C=C1 HQMCVCIGYWWYPC-UHFFFAOYSA-N 0.000 description 3
MOYWWURVFKMMSZ-UHFFFAOYSA-N 2-ethoxyethyl 2-(4-hydroxyphenoxy)propanoate Chemical compound CCOCCOC(=O)C(C)OC1=CC=C(O)C=C1 MOYWWURVFKMMSZ-UHFFFAOYSA-N 0.000 description 3
DPKWXRUINJHOOB-UHFFFAOYSA-N 4-(2-hydroxyethoxy)phenol Chemical compound OCCOC1=CC=C(O)C=C1 DPKWXRUINJHOOB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
DPBROXGZCCUJQD-UHFFFAOYSA-N 1-prop-2-enoxy-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(OCC=C)C=C1 DPBROXGZCCUJQD-UHFFFAOYSA-N 0.000 description 2
PWRCOONECNWDBH-UHFFFAOYSA-N 4-prop-2-enoxyphenol Chemical compound OC1=CC=C(OCC=C)C=C1 PWRCOONECNWDBH-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
150000008378 aryl ethers Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000539 dimer Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JLEJCNOTNLZCHQ-VKHMYHEASA-N methyl (2s)-2-chloropropanoate Chemical compound COC(=O)[C@H](C)Cl JLEJCNOTNLZCHQ-VKHMYHEASA-N 0.000 description 2
JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
HHSUZJHQRJCXDF-UHFFFAOYSA-N (4-hydroxyphenyl) ethaneperoxoate Chemical compound CC(=O)OOC1=CC=C(O)C=C1 HHSUZJHQRJCXDF-UHFFFAOYSA-N 0.000 description 1
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
XCTSGGVBLWBSIJ-UHFFFAOYSA-N 1-methoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=CC=C(C(C)=C)C=C1 XCTSGGVBLWBSIJ-UHFFFAOYSA-N 0.000 description 1
AMCMPYSRJBOXBL-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(O)C=C1 AMCMPYSRJBOXBL-UHFFFAOYSA-N 0.000 description 1
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 1
PJAIMBYNTXNOCN-UHFFFAOYSA-N 3,6-dibromo-1h-indole Chemical compound BrC1=CC=C2C(Br)=CNC2=C1 PJAIMBYNTXNOCN-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
SEHIFFDYECOUMU-UHFFFAOYSA-N CC(=C)C1=CC=C(O)C=C1.C=1C=C(O)C=CC=1C(C)(C)CC(=C)C1=CC=C(O)C=C1 Chemical compound CC(=C)C1=CC=C(O)C=C1.C=1C=C(O)C=CC=1C(C)(C)CC(=C)C1=CC=C(O)C=C1 SEHIFFDYECOUMU-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000011149 active material Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000007033 dehydrochlorination reaction Methods 0.000 description 1
125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
HDNZRSDOZLMRPQ-UHFFFAOYSA-N methyl 2-(4-prop-1-en-2-ylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(C(C)=C)C=C1 HDNZRSDOZLMRPQ-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000013022 venting Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/18—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups bound to carbon atoms of carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
- 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
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

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

DD84264435A 1983-06-24 1984-06-22 Verfahren zur herstellung von monoethern von dihydroxylbenzolen DD232484A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/507,448 US4511731A (en)	1983-06-24	1983-06-24	2-Ethoxyethyl 2-(4-hydroxyphenoxy)-propanoate

Publications (1)

Publication Number	Publication Date
DD232484A5 true DD232484A5 (de)	1986-01-29

Family

ID=24018694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84264435A DD232484A5 (de)	1983-06-24	1984-06-22	Verfahren zur herstellung von monoethern von dihydroxylbenzolen

Country Status (13)

Country	Link
US (1)	US4511731A (da)
EP (1)	EP0129851B1 (da)
JP (1)	JPS6051142A (da)
KR (1)	KR910002673B1 (da)
AU (1)	AU569892B2 (da)
BR (1)	BR8403065A (da)
CA (1)	CA1261869A (da)
DD (1)	DD232484A5 (da)
DE (1)	DE3472670D1 (da)
DK (1)	DK295184A (da)
ES (1)	ES8601086A1 (da)
IL (1)	IL72075A0 (da)
RO (1)	RO89960A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR3007971B1 (fr) *	2013-07-02	2016-07-15	Oreal	Utilisation de derives de l'acide 4-hydroxyphenoxy-acetique en tant qu'agents antioxydants et/ou antiradicalaires
CN105753656A (zh) *	2016-04-26	2016-07-13	张家港市三联化工科技有限公司	(r)-(+)-2-(4-羟基苯氧基)丙酸甲酯的合成方法
KR102794968B1 (ko) *	2024-10-18	2025-04-10	국방과학연구소	연속 흐름 반응에 의한 5,5'-비스테트라졸-1,1'-디올 디하이드레이트의 제조 방법

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS55127333A (en) *	1979-03-26	1980-10-02	Ihara Chem Ind Co Ltd	Preparation of substituted phenols
JPS55127332A (en) *	1979-03-26	1980-10-02	Ihara Chem Ind Co Ltd	Preparation of 4-substituted-isopropenylbenzene
JPS55127334A (en) *	1979-03-26	1980-10-02	Ihara Chem Ind Co Ltd	Preparation of substituted phenols
JPS55127331A (en) *	1979-03-26	1980-10-02	Ihara Chem Ind Co Ltd	Preparation of 4-methyl-2,4-bis(p-substituted-oxyphenyl) pent-1-ene
US4328361A (en) *	1981-01-16	1982-05-04	The Upjohn Company	Novel process

1983
- 1983-06-24 US US06/507,448 patent/US4511731A/en not_active Expired - Fee Related
1984
- 1984-06-06 CA CA000456031A patent/CA1261869A/en not_active Expired
- 1984-06-11 IL IL72075A patent/IL72075A0/xx unknown
- 1984-06-15 DK DK295184A patent/DK295184A/da not_active Application Discontinuation
- 1984-06-18 AU AU29463/84A patent/AU569892B2/en not_active Ceased
- 1984-06-20 EP EP84107119A patent/EP0129851B1/en not_active Expired
- 1984-06-20 DE DE8484107119T patent/DE3472670D1/de not_active Expired
- 1984-06-22 ES ES533635A patent/ES8601086A1/es not_active Expired
- 1984-06-22 BR BR8403065A patent/BR8403065A/pt unknown
- 1984-06-22 JP JP59129026A patent/JPS6051142A/ja active Pending
- 1984-06-22 DD DD84264435A patent/DD232484A5/de unknown
- 1984-06-22 KR KR1019840003521A patent/KR910002673B1/ko not_active Expired
- 1984-06-24 RO RO84114989A patent/RO89960A/ro unknown

Also Published As

Publication number	Publication date
AU2946384A (en)	1985-01-03
KR850001146A (ko)	1985-03-16
ES533635A0 (es)	1985-10-16
IL72075A0 (en)	1984-10-31
KR910002673B1 (ko)	1991-05-03
BR8403065A (pt)	1985-05-28
RO89960A (ro)	1986-09-30
EP0129851A2 (en)	1985-01-02
EP0129851B1 (en)	1988-07-13
AU569892B2 (en)	1988-02-25
CA1261869A (en)	1989-09-26
EP0129851A3 (en)	1985-10-02
ES8601086A1 (es)	1985-10-16
JPS6051142A (ja)	1985-03-22
DK295184D0 (da)	1984-06-15
US4511731A (en)	1985-04-16
DK295184A (da)	1984-12-25
DE3472670D1 (en)	1988-08-18

Publication	Publication Date	Title
EP0024612B1 (de)	1983-10-05	Neue 4-Fluor-3-phenoxy-benzyl-ether und Verfahren zu ihrer Herstellung und ihre Verwendung
EP0011091B1 (de)	1981-07-15	Verfahren zur Herstellung von Alkyl- bzw. Arylthiomethyl-phenolen
DD232484A5 (de)	1986-01-29	Verfahren zur herstellung von monoethern von dihydroxylbenzolen
EP0123187B1 (de)	1988-04-20	Verfahren zur Herstellung von fluorierten Phenylessigsäureestern und neue fluorierte Trichlorethylbenzole
DD206371A5 (de)	1984-01-25	Verfahren zur herstellung eines 2s chiralen alkohols
DE3915495A1 (de)	1990-11-15	Kernfluorierte trifluormethylbenzaldehyde
CA1261356A (en)	1989-09-26	Process for production of m-phenoxybenzyl alcohol
EP0888280A1 (de)	1999-01-07	Verfahren zur herstellung von 2-(2-methylphenyl)-3-methoxyacrylsäure-methylester
DE2652810C3 (de)	1979-05-10	Verfahren zur Herstellung von aromatischen Fluorverbindungen
EP0665212B1 (de)	1999-06-09	Verfahren zur Herstellung von 2,4,6-Trimethylphenylessigsäure
DE10026750A1 (de)	2001-01-18	Verfahren zur Herstellung von Retinin und Zwischenprodukte zur Herstellung desselben
DE3104388A1 (de)	1982-10-21	Verfahren zur herstellung von 1-alkyl-2-chlor-5-nitro-4-benzol-sulfonsaeuren
DD152537A5 (de)	1981-12-02	Verfahren zur herstellung von 4-fluor-3-phenoxy-toluol
EP0500639B1 (de)	1994-08-03	Verfahren zur herstellung von alkyl-[3-chlorphenyl]-sulfonen
DE19859684A1 (de)	2000-06-29	Verfahren zur Herstellung von Fluor enthaltenden Phenethylaminen sowie neue, Fluor enthalende beta-Iminovinyl- und beta-Iminoethylbenzole
EP0608714B1 (de)	1997-05-02	Verfahren zur Herstellung chlorierter 4,5-Difluorbenzoesäuren, -benzoesäurederivate und -benzaldehyde
DE19954936A1 (de)	2001-05-17	Verfahren zur Herstellung von Benzofuranonoximen
DE19546920A1 (de)	1997-06-19	Verfahren zur Herstellung synthetischer Pyrethroide durch azeotrope Veresterung
DE4225763A1 (de)	1994-02-10	Verfahren zur Herstellung von Halogenaromaten
EP0035635B1 (de)	1983-10-19	Verfahren zur Herstellung von Trimethylbenzochinon
US4691042A (en)	1987-09-01	Preparation of monaoalkylated dihydroxybenzenes and novel compounds prepared thereby
EP0128489B1 (de)	1989-11-29	Verfahren zur Herstellung von Succinylobernsteinsäuredialkylestern
EP1384706A1 (de)	2004-01-28	Verfahren zur Monoalkylierung C-H-acider Methylengruppen
DE3909213A1 (de)	1990-10-11	Halogenbenzolderivate
CH650488A5 (de)	1985-07-31	Verfahren zur herstellung des m-phenoxy-benzyl-alkohols.