IL40384A - Process for the preparation of 2,5-dialkyl-5-aralkoxy-1,3-dioxanes - Google Patents
Process for the preparation of 2,5-dialkyl-5-aralkoxy-1,3-dioxanesInfo
- Publication number
- IL40384A IL40384A IL40384A IL4038472A IL40384A IL 40384 A IL40384 A IL 40384A IL 40384 A IL40384 A IL 40384A IL 4038472 A IL4038472 A IL 4038472A IL 40384 A IL40384 A IL 40384A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- substituent
- substituted
- aralkoxy
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- 150000002118 epoxides Chemical class 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 239000004593 Epoxy Substances 0.000 claims abstract 2
- -1 aralkyl halide Chemical class 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1412974 5 - Substituted - 5 - hydroxy (or aralkoxy)-1,3-dioxenes FMC CORP 11 Oct 1972 [12 Oct 1971] 46748/72 Heading C2C [Also in Division A5] The invention comprises compounds (I): where R is haloalkyl and R<SP>1</SP> is hydrogen or C 1-4 alkyl and the preparation of 5-alkyl-5-aralkyloxy-1,3-dioxanes having a 2-substituent in cisrelationship to the 5-aralkoxy group by epoxidizing the double bond of a 2-substituted-5- alkylidene-1,3-dioxan, hydrogenolysing the resulting epoxide, in which there is a cis relationship between the epoxy oxygen and the 2- substituent to form a 2-substituted-5-hydroxy 5-alkyl- 1,3-dioxane and etherifying the latter with an aralkyl halide. The 5 - alkyl - 5 - aralkoxy - 1,3 - dioxanes have herbicidal properties and may be used in herbicidal compositions.
[GB1412974A]
Claims (6)
1. Process for the production of 5-alkyl-5-aralkoxy-l,3-dioxanes having a 2-substituent in cis relationship to the 5- » . , ' '* ' ·. aralfeoxy group, characterized by epoxidizing the double bond of a . ·/?' 2-substituted-5-alkylidene-l,3-dioxane to form an epoxide in which there is a cis relationship between the epoxy oxygen (on the 5-carbon of the 1,3-dioxane) and the 2-substituent, hydrogenolyzing said epoxide to form a 2-substituted-5-hydroxy-5-alkyl-1,3-dioxane in which there is a cis relationship between the 5-hydroxy and ♦he 2-substituent, and etherifying said 2-substituted-5-hydroxy-5-alkyl- ,3-dioxane with an aralkyl halide, wherein the 2-substituent is lower alk l or lower haloalkyl, the 5-alkyl is lower alkyl, and the 5-aralkoxy group is benzyloxy which may be substituted in the benzene nucleus by halogen or lower alkyl, , ^
2. Process as in claim 1 in which said 2-substituent is ethyl.
3. j Process as in claim 1 in which alkylidene is methylene.
4. Process as in claim 1 in which said epoxidation is effected with an epoxidizing agent comprising hydrogen peroxide and benzonitrile.
5. Process as in claim 1 in which said hydrogenation is effected by reacting the epoxide with hydrogen in the presence of a solid hydrogenation catalyst.
6. Process as in claim 1 in which said hydrogenation is effected by reacting the epoxide with hydrogen in the presence of a solid metal hydrogenation catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18797171A | 1971-10-12 | 1971-10-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40384A0 IL40384A0 (en) | 1972-11-28 |
| IL40384A true IL40384A (en) | 1976-07-30 |
Family
ID=22691255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40384A IL40384A (en) | 1971-10-12 | 1972-09-17 | Process for the preparation of 2,5-dialkyl-5-aralkoxy-1,3-dioxanes |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4844266A (en) |
| AT (1) | AT326122B (en) |
| AU (1) | AU473478B2 (en) |
| BE (1) | BE789905A (en) |
| CH (1) | CH578551A5 (en) |
| DE (1) | DE2247030A1 (en) |
| ES (1) | ES407540A1 (en) |
| FR (1) | FR2156206B1 (en) |
| GB (1) | GB1412974A (en) |
| HU (1) | HU165917B (en) |
| IE (1) | IE36718B1 (en) |
| IL (1) | IL40384A (en) |
| IT (1) | IT986854B (en) |
| NL (1) | NL7213829A (en) |
| PL (1) | PL83596B1 (en) |
| RO (1) | RO64143A (en) |
| SU (1) | SU524518A3 (en) |
| ZA (1) | ZA726332B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081459A (en) * | 1969-11-14 | 1978-03-28 | Produits Chimiques Ugine Kuhlmann | Trioxa-1, 5, 7 spiro [2,5] octanes and their method of preparation |
| US4527126A (en) * | 1983-08-26 | 1985-07-02 | Micro Component Technology, Inc. | AC parametric circuit having adjustable delay lock loop |
| US4554011A (en) * | 1984-08-24 | 1985-11-19 | Chevron Research Company | Herbicidal 2S-(2β,4β,5β)-5-Arylmethoxy-4-substituted 2-alkyl-1,3-dioxane derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758352A (en) * | 1969-11-14 | 1971-04-16 | Ugine Kuhlmann | NEW TRIOXA-1,5,7 SPIRO (2.5) OCTANES AND THEIR PREPARATION |
-
0
- BE BE789905D patent/BE789905A/en unknown
-
1972
- 1972-09-14 AU AU46650/72A patent/AU473478B2/en not_active Expired
- 1972-09-15 ZA ZA726332A patent/ZA726332B/en unknown
- 1972-09-17 IL IL40384A patent/IL40384A/en unknown
- 1972-09-19 IE IE1279/72A patent/IE36718B1/en unknown
- 1972-09-26 DE DE19722247030 patent/DE2247030A1/en active Pending
- 1972-10-06 SU SU1835483A patent/SU524518A3/en active
- 1972-10-09 AT AT865672A patent/AT326122B/en not_active IP Right Cessation
- 1972-10-10 IT IT30321/72A patent/IT986854B/en active
- 1972-10-10 PL PL1972158180A patent/PL83596B1/pl unknown
- 1972-10-10 FR FR7235806A patent/FR2156206B1/fr not_active Expired
- 1972-10-11 CH CH1482072A patent/CH578551A5/xx not_active IP Right Cessation
- 1972-10-11 JP JP47101208A patent/JPS4844266A/ja active Pending
- 1972-10-11 ES ES407540A patent/ES407540A1/en not_active Expired
- 1972-10-11 GB GB4674872A patent/GB1412974A/en not_active Expired
- 1972-10-12 NL NL7213829A patent/NL7213829A/xx unknown
- 1972-10-12 RO RO7200072495A patent/RO64143A/en unknown
- 1972-10-12 HU HUFA927A patent/HU165917B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2156206B1 (en) | 1977-12-23 |
| AU4665072A (en) | 1974-03-21 |
| GB1412974A (en) | 1975-11-05 |
| NL7213829A (en) | 1973-04-16 |
| ATA865672A (en) | 1975-02-15 |
| AU473478B2 (en) | 1976-06-24 |
| ES407540A1 (en) | 1976-01-16 |
| IE36718B1 (en) | 1977-02-02 |
| SU524518A3 (en) | 1976-08-05 |
| RO64143A (en) | 1978-10-15 |
| JPS4844266A (en) | 1973-06-26 |
| ZA726332B (en) | 1973-06-27 |
| BE789905A (en) | 1973-04-10 |
| PL83596B1 (en) | 1975-12-31 |
| IE36718L (en) | 1973-04-12 |
| FR2156206A1 (en) | 1973-05-25 |
| IL40384A0 (en) | 1972-11-28 |
| HU165917B (en) | 1974-12-28 |
| DE2247030A1 (en) | 1973-04-19 |
| AT326122B (en) | 1975-11-25 |
| CH578551A5 (en) | 1976-08-13 |
| IT986854B (en) | 1975-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR890012981A (en) | Azole derivatives, their preparation and agricultural and horticultural chemicals containing them | |
| GB1369252A (en) | Oxabicyclooctane derivatives | |
| GB799269A (en) | Production of intermediates for the synthesis of reserpine and related compounds | |
| KR830007550A (en) | Method for preparing cyclic amine | |
| IL40384A (en) | Process for the preparation of 2,5-dialkyl-5-aralkoxy-1,3-dioxanes | |
| US4057589A (en) | Hydroxylation of unsaturated diols to prepare novel tetraols | |
| GB1364106A (en) | Phenoxyalkylamines process for their preparation and applications thereof | |
| DE3722486A1 (en) | NEW EPOXY REAGENT AND ITS USE | |
| GB1527258A (en) | Process for the preparation of polyepoxides | |
| IE35956L (en) | Fused ring indole derivatives | |
| GB1424284A (en) | Catalyst for producing oxirane compounds by epoxidizing olefins with hydroperoxides | |
| GB1498365A (en) | Process for preparing 3-oxy-4h-pyran-4-one derivatives | |
| GB1133313A (en) | Production of styrenes and of oxirane compounds | |
| Bapat et al. | Nitrones and oxazirans. III. Photolysis of 1-pyrroline 1-oxides and their related oxazirans | |
| Delpech et al. | Retrosynthetic studies with forskolin | |
| GB1448873A (en) | Ring a -aromatic 13,17-epoxy steroids | |
| US3821242A (en) | Diglycidyl ethers | |
| GB1422473A (en) | Chloroacetanilides for regulating plant growth | |
| GB1166557A (en) | A Process for the Production of Unsaturated Alcohols | |
| GB1185137A (en) | Novel Epoxides and Cured Polymers obtained therefrom | |
| US2883396A (en) | Hemiacetal ester epoxides | |
| GB1422444A (en) | 10-substituted-benzocycloheptathiophenone derivatives | |
| US2885398A (en) | 17alpha-alkyltestosterone derivatives | |
| GB1128141A (en) | New epoxy compounds, process for their preparation and their use | |
| US4267395A (en) | 2-Decarboxy-2-hydroxymethyl-19-hydroxy-19-methyl-6A-carba-PGI2 compounds |