IL90704A - Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene) - Google Patents

Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene)

Info

Publication number: IL90704A
Authority: IL; Israel
Prior art keywords: accordance; stage; propyl; solvent; amine
Prior art date: 1989-06-21

Application number

IL9070489A

Other languages

English (en)

Hebrew (he)

Other versions

IL90704A0 (en

Inventor

Joseph Sharvit

Abraham Adolf Pereferkovich

Original Assignee

Makhteshim Chem Works Ltd

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.)

1989-06-21

Filing date

1989-06-21

Publication date

1994-10-07

1989-06-21 Application filed by Makhteshim Chem Works Ltd filed Critical Makhteshim Chem Works Ltd

1989-06-21 Priority to IL9070489A priority Critical patent/IL90704A/en

1990-01-18 Publication of IL90704A0 publication Critical patent/IL90704A0/xx

1990-06-13 Priority to ZA904573A priority patent/ZA904573B/xx

1990-06-13 Priority to DE69011977T priority patent/DE69011977T2/de

1990-06-13 Priority to AT90111202T priority patent/ATE110710T1/de

1990-06-13 Priority to EP90111202A priority patent/EP0403952B1/de

1990-06-13 Priority to HU923863A priority patent/HU207984B/hu

1990-06-13 Priority to HU903824A priority patent/HU207709B/hu

1990-06-14 Priority to US07/537,972 priority patent/US5093526A/en

1994-10-07 Publication of IL90704A publication Critical patent/IL90704A/en

Links

238000000034 method Methods 0.000 title claims description 43
CLFQSOIBYICELN-UHFFFAOYSA-N n-[2-(2,4,6-trichlorophenoxy)ethyl]propan-1-amine Chemical compound CCCNCCOC1=C(Cl)C=C(Cl)C=C1Cl CLFQSOIBYICELN-UHFFFAOYSA-N 0.000 title abstract description 4
239000002904 solvent Substances 0.000 claims abstract description 37
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims abstract description 16
-1 tetra-alkyl ammonium halide Chemical class 0.000 claims abstract description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 14
VQUYNUJARXBNPK-UHFFFAOYSA-N 2-chloroethoxybenzene Chemical compound ClCCOC1=CC=CC=C1 VQUYNUJARXBNPK-UHFFFAOYSA-N 0.000 claims abstract description 11
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims abstract description 7
FBRGWNDXBBWEHK-UHFFFAOYSA-N n-(2-phenoxyethyl)propan-1-amine Chemical compound CCCNCCOC1=CC=CC=C1 FBRGWNDXBBWEHK-UHFFFAOYSA-N 0.000 claims abstract description 7
229960005323 phenoxyethanol Drugs 0.000 claims abstract description 7
230000003197 catalytic effect Effects 0.000 claims abstract description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
239000000460 chlorine Substances 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 17
150000001412 amines Chemical class 0.000 claims description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
239000004202 carbamide Substances 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
235000019270 ammonium chloride Nutrition 0.000 claims 3
125000005207 tetraalkylammonium group Chemical group 0.000 claims 3
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 2
229960003750 ethyl chloride Drugs 0.000 claims 2
PRDUHXPVDHDGKN-UHFFFAOYSA-N tetrachloromethane;hydrate Chemical compound O.ClC(Cl)(Cl)Cl PRDUHXPVDHDGKN-UHFFFAOYSA-N 0.000 claims 2
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical group C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 claims 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 claims 1
239000012046 mixed solvent Substances 0.000 claims 1
239000005820 Prochloraz Substances 0.000 description 6
TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 6
231100000331 toxic Toxicity 0.000 description 6
230000002588 toxic effect Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000244317 Tillandsia usneoides Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000000711 cancerogenic effect Effects 0.000 description 2
231100000315 carcinogenic Toxicity 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
150000004899 1,4-dioxins Chemical class 0.000 description 1
LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
101150052863 THY1 gene Proteins 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000006165 cyclic alkyl group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002013 dioxins Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

IL9070489A 1989-06-21 1989-06-21 Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene) IL90704A (en)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
IL9070489A IL90704A (en)	1989-06-21	1989-06-21	Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene)
ZA904573A ZA904573B (en)	1989-06-21	1990-06-13	An environmentally safe method of preparing a certain dialkylamine
DE69011977T DE69011977T2 (de)	1989-06-21	1990-06-13	In bezug auf die Umwelt sicheres Verfahren zur Herstellung eines bestimmten Dialkylamins.
AT90111202T ATE110710T1 (de)	1989-06-21	1990-06-13	In bezug auf die umwelt sicheres verfahren zur herstellung eines bestimmten dialkylamins.
EP90111202A EP0403952B1 (de)	1989-06-21	1990-06-13	In bezug auf die Umwelt sicheres Verfahren zur Herstellung eines bestimmten Dialkylamins
HU923863A HU207984B (en)	1989-06-21	1990-06-13	Process for producing n-/n-propyl/-n-/2-phenoxy-ethyl/-amine
HU903824A HU207709B (en)	1989-06-21	1990-06-13	Process for producing n-/n-propyl/-n-/2-/2,4,6-trichloro-phenoxy/-ethyl/-amine
US07/537,972 US5093526A (en)	1989-06-21	1990-06-14	Environmentally safe method of preparing a certain dialkylamine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL9070489A IL90704A (en)	1989-06-21	1989-06-21	Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene)

Publications (2)

Publication Number	Publication Date
IL90704A0 IL90704A0 (en)	1990-01-18
IL90704A true IL90704A (en)	1994-10-07

Family

ID=11060075

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9070489A IL90704A (en)	1989-06-21	1989-06-21	Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene)

Country Status (7)

Country	Link
US (1)	US5093526A (de)
EP (1)	EP0403952B1 (de)
AT (1)	ATE110710T1 (de)
DE (1)	DE69011977T2 (de)
HU (2)	HU207709B (de)
IL (1)	IL90704A (de)
ZA (1)	ZA904573B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL106118A (en) *	1993-06-24	1997-08-14	Agan Chemical Manufacturers	Process for preparing n-alkyl-3,4-dialkyl- 2,6-dinitro- anilines and intermediates thereof
SE9704834D0 (sv) *	1997-12-22	1997-12-22	Astra Ab	New process
CN100340550C (zh) *	2005-09-16	2007-10-03	华南师范大学	咪酰胺的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1469772A (en) *	1973-06-21	1977-04-06	Boots Co Ltd	Fungicidal imidazole derivatives
US4504484A (en) *	1982-11-04	1985-03-12	Chevron Research Company	Certain N,N-di-substituted-pyridine carboxamides, fungicidal compositions and fungicidal method of use
GB8609904D0 (en) *	1986-04-23	1986-05-29	Fbc Ltd	Preparation of metal phenates
GB8714920D0 (en) *	1987-06-25	1987-07-29	Shell Int Research	Thiazole derivatives

1989
- 1989-06-21 IL IL9070489A patent/IL90704A/en not_active IP Right Cessation
1990
- 1990-06-13 DE DE69011977T patent/DE69011977T2/de not_active Expired - Fee Related
- 1990-06-13 AT AT90111202T patent/ATE110710T1/de not_active IP Right Cessation
- 1990-06-13 HU HU903824A patent/HU207709B/hu not_active IP Right Cessation
- 1990-06-13 EP EP90111202A patent/EP0403952B1/de not_active Expired - Lifetime
- 1990-06-13 ZA ZA904573A patent/ZA904573B/xx unknown
- 1990-06-13 HU HU923863A patent/HU207984B/hu not_active IP Right Cessation
- 1990-06-14 US US07/537,972 patent/US5093526A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HU903824D0 (en)	1990-11-28
HU207709B (en)	1993-05-28
DE69011977T2 (de)	1995-03-30
US5093526A (en)	1992-03-03
ZA904573B (en)	1992-01-29
EP0403952A3 (de)	1992-02-12
ATE110710T1 (de)	1994-09-15
DE69011977D1 (de)	1994-10-06
HU9203863D0 (en)	1993-03-29
EP0403952B1 (de)	1994-08-31
IL90704A0 (en)	1990-01-18
HUT53864A (en)	1990-12-28
HU207984B (en)	1993-07-28
EP0403952A2 (de)	1990-12-27

Legal Events

Date	Code	Title	Description
2000-06-29	RH	Patent void

Publication	Publication Date	Title
US4314086A (en)	1982-02-02	Preparation of aliphatic/aromatic ethers
IL90704A (en)	1994-10-07	Method for the preparation of N-N-) 2,4,6-trichlorophenoxy (environmentally reliable ethylene)
EP0147472B1 (de)	1988-10-12	4-chlor-4-methyl-5-methylen-1,3-dioxolan-2-on
US5057633A (en)	1991-10-15	Synthesis of perfluoroalkyl bromides
US6353126B1 (en)	2002-03-05	Process for the production of malononitrile
US5091577A (en)	1992-02-25	Method of preparing fungicidal intermediates
JPH0745442B2 (ja)	1995-05-17	ハロゲン化第４級アンモニウム化合物の製造法
US5091578A (en)	1992-02-25	Method of preparing phenoxy ethers for use as agrochemical intermediates
US4293702A (en)	1981-10-06	Method for preparing 4-substituted-N-methylbenzothiazolone derivatives
KR100619386B1 (ko)	2006-09-06	할로겐화 페닐말로네이트의 제조방법
US5510509A (en)	1996-04-23	Preparation of esters of cyclopropane-1,1-dicarboxylic acid
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IL90702A (en)	1994-10-07	Method of preparing n-n-propyl-n-2-(2,4,6-trichloro-phenoxy)-ethyl amine
KR820001888B1 (ko)	1982-10-18	N-알킬벤조티아졸론 유도체의 제조방법
US6037509A (en)	2000-03-14	Process for producing 1-bromo-4-phenylbutane
JPH08239338A (ja)	1996-09-17	メチル−１，１−ジクロロメチルエーテルまたはエチル−１，１−ジクロロメチルエーテルの合成方法
EP0307106B1 (de)	1992-01-15	P-oder m-tert-Butoxyphenethylalkohol und Verfahren zu dessen Herstellung
US6706917B1 (en)	2004-03-16	Preparing method of 2-phenylalkanoic acid derivatives
GB2036720A (en)	1980-07-02	Preparation of tetrachloro or tetrabromo cyclohexanone
KR850001529B1 (ko)	1985-10-16	아미노산의 페놀에스테르 유도체의 제조방법
KR830002719B1 (ko)	1983-12-09	피레드로이드계 살충제 제조방법
EP0199506A2 (de)	1986-10-29	Verfahren zur Herstellung von Alkylhalogeniden
US20140336404A1 (en)	2014-11-13	Method for producing pentafluorosulfanyl benzoic acid
KR19980032426A (ko)	1998-07-25	아민 제조방법
JPH082895B2 (ja)	1996-01-17	チオフェンジカルボン酸ジエステルを製造する方法