DD145752A5 - Verfahren zur herstellung von 2,4,4-trimethyl-3-carbalko?y-5-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen sowie von 2,5,5-trimethyl-3-carbalkoxy-4-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen - Google Patents

Verfahren zur herstellung von 2,4,4-trimethyl-3-carbalko?y-5-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen sowie von 2,5,5-trimethyl-3-carbalkoxy-4-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen Download PDF

Info

Publication number: DD145752A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; reaction; items; trimethyl; beta
Prior art date: 1977-09-08

Application number

DD78215278A

Other languages

German (de)

English (en)

Inventor

Hans-Georg Schmidt

Original Assignee

Dynamit Nobel Ag

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.)

1977-09-08

Filing date

1978-09-01

Publication date

1981-01-07

1977-09-08 Priority claimed from DE19772740479 external-priority patent/DE2740479A1/de

1978-03-23 Priority claimed from DE19782812673 external-priority patent/DE2812673A1/de

1978-03-23 Priority claimed from DE19782812672 external-priority patent/DE2812672A1/de

1978-06-09 Priority claimed from DE19782825363 external-priority patent/DE2825363A1/de

1978-09-01 Application filed by Dynamit Nobel Ag filed Critical Dynamit Nobel Ag

1981-01-07 Publication of DD145752A5 publication Critical patent/DD145752A5/de

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 11
238000006243 chemical reaction Methods 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 18
239000003054 catalyst Substances 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 10
JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
238000004821 distillation Methods 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
238000009835 boiling Methods 0.000 claims description 6
230000008707 rearrangement Effects 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims 3
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000001149 thermolysis Methods 0.000 description 9
238000004508 fractional distillation Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 5
239000010453 quartz Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
-1 AlClO Chemical class 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
230000007717 exclusion Effects 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 3
238000007700 distillative separation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
238000012856 packing Methods 0.000 description 3
239000002728 pyrethroid Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
VNIRPUMAEZAXLI-UHFFFAOYSA-N 1,1,1-trichloro-4-methylpent-3-en-2-ol Chemical compound CC(C)=CC(O)C(Cl)(Cl)Cl VNIRPUMAEZAXLI-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
239000000919 ceramic Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
CCSGUWPRSWZQIO-UHFFFAOYSA-N 1,1,1-tribromo-4-methylpent-3-en-2-ol Chemical compound CC(C)=CC(O)C(Br)(Br)Br CCSGUWPRSWZQIO-UHFFFAOYSA-N 0.000 description 1
LWWJZSNCITZYEB-UHFFFAOYSA-N 1,1,1-trichloro-4-methylpent-4-en-2-ol Chemical compound CC(=C)CC(O)C(Cl)(Cl)Cl LWWJZSNCITZYEB-UHFFFAOYSA-N 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000013459 approach Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001942 cyclopropanes Chemical class 0.000 description 1
238000011161 development Methods 0.000 description 1
150000002012 dioxanes Chemical class 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
150000002835 noble gases Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S204/00—Chemistry: electrical and wave energy
- Y10S204/90—Effecting a change in isomerization by wave energy

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD78215278A 1977-09-08 1978-09-01 Verfahren zur herstellung von 2,4,4-trimethyl-3-carbalko?y-5-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen sowie von 2,5,5-trimethyl-3-carbalkoxy-4-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen DD145752A5 (de)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19772740479 DE2740479A1 (de)	1977-09-08	1977-09-08	2,4,4-trimethyl-3-carbalkoxy-5(beta,beta-dihalogenvinyl)-4,5-dihydrofurane
DE19782812673 DE2812673A1 (de)	1978-03-23	1978-03-23	2,5,5-trimethyl-3-carbalkoxy-4-(beta, beta-dihalogenvinyl)-4,5-dihydrofurane
DE19782812672 DE2812672A1 (de)	1978-03-23	1978-03-23	Verfahren zur herstellung von dihalogenvinylcyclopropancarbonsaeureestern
DE19782825363 DE2825363A1 (de)	1978-06-09	1978-06-09	Verfahren zur herstellung von 2,4,4-trimethyl-3-carbalkoxy-5-( beta, beta -dihalogenvinyl)-4,5-dihydrofurane

Publications (1)

Publication Number	Publication Date
DD145752A5 true DD145752A5 (de)	1981-01-07

Family

ID=27432249

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD78215278A DD145752A5 (de)	1977-09-08	1978-09-01	Verfahren zur herstellung von 2,4,4-trimethyl-3-carbalko?y-5-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen sowie von 2,5,5-trimethyl-3-carbalkoxy-4-(beta,beta-dihalogenvinyl)-4,5-dihydrofuranen
DD78207607A DD138899A5 (de)	1977-09-08	1978-09-01	Verfahren zur herstellung von dihalogenvinylcyclopropancarbonsaeureestern

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD78207607A DD138899A5 (de)	1977-09-08	1978-09-01	Verfahren zur herstellung von dihalogenvinylcyclopropancarbonsaeureestern

Country Status (13)

Country	Link
US (1)	US4180446A (es)
JP (1)	JPS5452061A (es)
AU (1)	AU3965678A (es)
BR (1)	BR7805844A (es)
DD (2)	DD145752A5 (es)
DK (1)	DK396278A (es)
ES (1)	ES473164A1 (es)
FR (1)	FR2402652A1 (es)
GB (1)	GB2005666B (es)
NL (1)	NL7809153A (es)
NO (1)	NO783051L (es)
PL (1)	PL209440A1 (es)
SE (1)	SE7809093L (es)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3509197A (en) *	1966-05-11	1970-04-28	Minnesota Mining & Mfg	Fluoro-containing cyclopropanes
US3674832A (en) *	1968-08-22	1972-07-04	Schering Corp	Cyclopropane carboxylic acid derivatives
SE366022B (es) *	1969-03-24	1974-04-08	Sumitomo Chemical Co

1978
- 1978-08-28 US US05/937,622 patent/US4180446A/en not_active Expired - Lifetime
- 1978-08-29 SE SE7809093A patent/SE7809093L/xx unknown
- 1978-09-01 DD DD78215278A patent/DD145752A5/de unknown
- 1978-09-01 DD DD78207607A patent/DD138899A5/xx unknown
- 1978-09-06 PL PL20944078A patent/PL209440A1/xx unknown
- 1978-09-06 FR FR7825620A patent/FR2402652A1/fr not_active Withdrawn
- 1978-09-06 BR BR7805844A patent/BR7805844A/pt unknown
- 1978-09-07 AU AU39656/78A patent/AU3965678A/en active Pending
- 1978-09-07 NO NO783051A patent/NO783051L/no unknown
- 1978-09-07 DK DK396278A patent/DK396278A/da unknown
- 1978-09-07 NL NL7809153A patent/NL7809153A/xx not_active Application Discontinuation
- 1978-09-07 JP JP10918878A patent/JPS5452061A/ja active Pending
- 1978-09-07 GB GB7835978A patent/GB2005666B/en not_active Expired
- 1978-09-07 ES ES473164A patent/ES473164A1/es not_active Expired

Also Published As

Publication number	Publication date
PL209440A1 (pl)	1979-06-04
FR2402652A1 (fr)	1979-04-06
AU3965678A (en)	1980-03-13
DK396278A (da)	1979-03-09
GB2005666B (en)	1982-03-03
US4180446A (en)	1979-12-25
GB2005666A (en)	1979-04-25
BR7805844A (pt)	1979-04-24
SE7809093L (sv)	1979-03-09
ES473164A1 (es)	1979-11-16
JPS5452061A (es)	1979-04-24
NL7809153A (nl)	1979-03-12
NO783051L (no)	1979-03-09
DD138899A5 (de)	1979-11-28

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US4853473A (en)	1989-08-01	Preparation of 2(5H)-furanones
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Burger et al.	2001	Domino Reactions with 2-Fluoro-3-trifluoromethylfurans and-thiophenes [1]
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EP0081090A1 (de)	1983-06-15	Verfahren zur Herstellung von 3,4-Dihydro-alpha-pyronen
EP0018533A1 (de)	1980-11-12	Substituierte Pentan-(oder Penten-)-carbonsäuren und ihre Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 3-(Aryl-vinyl)-2,2-dimethyl-cyclopropan-1-carbonsäureestern
US4198342A (en)	1980-04-15	Method of preparing dihalogen vinyl cyclopropanecarboxylic acid esters
DE2413823C2 (de)	1983-02-03	Verfahren zur Herstellung von tertiären Methylphosphinoxiden
US4198341A (en)	1980-04-15	2,5,5-Trimethyl-3-carbalkoxy-4(β,β-dihalovinyl)-4,5-dihydrofurans
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DE69434654T2 (de)	2006-08-03	Herstellung von Cyclopropanestern