ES8402807A1 - Process for the preparation of wherein (7E,9Z)-alkadienol derivatives - Google Patents
Process for the preparation of wherein (7E,9Z)-alkadienol derivativesInfo
- Publication number
- ES8402807A1 ES8402807A1 ES512230A ES512230A ES8402807A1 ES 8402807 A1 ES8402807 A1 ES 8402807A1 ES 512230 A ES512230 A ES 512230A ES 512230 A ES512230 A ES 512230A ES 8402807 A1 ES8402807 A1 ES 8402807A1
- Authority
- ES
- Spain
- Prior art keywords
- image
- reacting
- alkadienol
- derivatives
- preparation
- 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
- 238000000034 method Methods 0.000 title abstract 2
- BSAIUMLZVGUGKX-UHFFFAOYSA-N non-2-enal Chemical compound CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 241001261104 Lobesia botrana Species 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- -1 halide ion Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical class CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(7E,9Z)-alkadienol derivatives (I), < IMAGE > wherein R1 represents a lower alkyl group, and R2 represents a hydrogen atom or a lower acyl group are prepared by reacting a nonanal derivative (II), OHC-(CH2)7-CH2-OR2 (II> with an aliphatic alcohol halogenating the acetal (III) thus-obtained, < IMAGE > wherein R3 and R4 independently represent a lower alkyl group or together represent an ethylene group, treating the 2-halo-1,1-dialkoxynonane (IV) thus-obtained, < IMAGE > wherein X represents halogen, with a base treating the nonene derivative (V) thus-obtained, < IMAGE > with an acid, and reacting the nonenal (VI) thus-obtained, < IMAGE > with an alkyl-triphenylphosphonium halide (VII), < IMAGE > wherein X<(-)> represents a halide ion, in the presence of a base, in an apolar or dipolar solvent, under inert gas. This provides an economic process for the preparation of the compounds of the general formula (I) which produce a significantly strong stimulating reaction on male European grape vine moth.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU811358A HU181328B (en) | 1981-05-15 | 1981-05-15 | Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
ES8402807A1 true ES8402807A1 (en) | 1984-03-01 |
ES512230A0 ES512230A0 (en) | 1984-03-01 |
Family
ID=10954100
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES512230A Granted ES512230A0 (en) | 1981-05-15 | 1982-05-14 | "PROCEDURE FOR PREPARATION OF DERIVATIVES (7E, 9Z) -ALCADIENOLES". |
Country Status (10)
Country | Link |
---|---|
BE (1) | BE893152A (en) |
CS (1) | CS226740B2 (en) |
ES (1) | ES512230A0 (en) |
FR (1) | FR2505820B1 (en) |
GB (1) | GB2098609B (en) |
GR (1) | GR76012B (en) |
HU (1) | HU181328B (en) |
IT (1) | IT1190823B (en) |
SU (1) | SU1356957A3 (en) |
YU (1) | YU101782A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3721536A1 (en) * | 1986-07-18 | 1988-01-21 | Basf Ag | Method and composition for controlling the grape berry moth |
DE3726511A1 (en) * | 1987-08-08 | 1989-02-16 | Basf Ag | 1,1-DIALKOXY- OR 1,1 - ((ALPHA), (OMEGA) -METHYLENE DIXY) -NON-2-IN-9-OL AND THEIR OH-PROTECTED DERIVATIVES |
DE3729225A1 (en) * | 1987-09-02 | 1989-03-23 | Basf Ag | 9-HYDROXYDODEC-10-ENYL-1-T-BUTYL ETHER AND ITS USE AS AN INTERMEDIATE PRODUCT FOR THE SYNTHESIS OF 8,10-DODECADIENOL |
DE3815044A1 (en) * | 1988-05-04 | 1989-11-16 | Basf Ag | 1-TERT.-BUTOXY- (OMEGA) -ALKENES AND THEIR USE AS FRAGRANCES |
DE3815043A1 (en) * | 1988-05-04 | 1989-11-16 | Basf Ag | 3,9-DIHYDROXYNONIN AND DERIVATIVES PROTECTED AT THE 9-OH FUNCTION |
DE3817399A1 (en) * | 1988-05-21 | 1989-11-30 | Basf Ag | METHOD FOR PRODUCING E7 / Z9-ALKADIEN-1-OLEN AND THEIR DERIVATIVES PROTECTED ON THE HYDROXYL GROUP |
US6838576B1 (en) * | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3845108A (en) * | 1973-08-31 | 1974-10-29 | W Roelofs | Trans-7-cis-9-dodecadien-1-yl acetate |
FR2267705A1 (en) * | 1974-04-19 | 1975-11-14 | Anvar | 1-Acetoxy-7,9-dodecadiene - sexual attraction for insect pests |
US3954818A (en) * | 1974-11-25 | 1976-05-04 | Zoecon Corporation | Synthesis of non-4-en-6-ynoic acid ester |
FR2341546A1 (en) * | 1976-02-20 | 1977-09-16 | Anvar | Prepn. of E,Z-dienes including insect pheromones - starting from alpha-cyclopropyl alpha-alkynyl alcohols |
-
1981
- 1981-05-15 HU HU811358A patent/HU181328B/en not_active IP Right Cessation
-
1982
- 1982-05-12 BE BE1/10513A patent/BE893152A/en not_active IP Right Cessation
- 1982-05-13 FR FR8208332A patent/FR2505820B1/en not_active Expired
- 1982-05-13 GB GB8213990A patent/GB2098609B/en not_active Expired
- 1982-05-13 CS CS823484A patent/CS226740B2/en unknown
- 1982-05-13 YU YU01017/82A patent/YU101782A/en unknown
- 1982-05-14 IT IT21254/82A patent/IT1190823B/en active
- 1982-05-14 SU SU823441301A patent/SU1356957A3/en active
- 1982-05-14 GR GR68156A patent/GR76012B/el unknown
- 1982-05-14 ES ES512230A patent/ES512230A0/en active Granted
Also Published As
Publication number | Publication date |
---|---|
CS226740B2 (en) | 1984-04-16 |
FR2505820B1 (en) | 1985-11-15 |
BE893152A (en) | 1982-11-12 |
FR2505820A1 (en) | 1982-11-19 |
GB2098609B (en) | 1985-08-14 |
YU101782A (en) | 1985-06-30 |
GR76012B (en) | 1984-08-03 |
SU1356957A3 (en) | 1987-11-30 |
IT1190823B (en) | 1988-02-24 |
ES512230A0 (en) | 1984-03-01 |
GB2098609A (en) | 1982-11-24 |
HU181328B (en) | 1983-07-28 |
IT8221254A0 (en) | 1982-05-14 |
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