JPS63119480A - Production of gamma-jasmolactone - Google Patents
Production of gamma-jasmolactoneInfo
- Publication number
- JPS63119480A JPS63119480A JP26358686A JP26358686A JPS63119480A JP S63119480 A JPS63119480 A JP S63119480A JP 26358686 A JP26358686 A JP 26358686A JP 26358686 A JP26358686 A JP 26358686A JP S63119480 A JPS63119480 A JP S63119480A
- Authority
- JP
- Japan
- Prior art keywords
- cis
- reaction
- acrylaldehyde
- acetal
- jasmolactone
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- NKNGVPNCSFZRSM-ONEGZZNKSA-N 5-(3-hexenyl)dihydro-2(3h)-furanone Chemical compound CC\C=C\CCC1CCC(=O)O1 NKNGVPNCSFZRSM-ONEGZZNKSA-N 0.000 title claims description 13
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001241 acetals Chemical class 0.000 claims abstract description 12
- 239000003810 Jones reagent Substances 0.000 claims abstract description 5
- 238000007342 radical addition reaction Methods 0.000 claims abstract description 5
- MCIPQLOKVXSHTD-UHFFFAOYSA-N 3,3-diethoxyprop-1-ene Chemical compound CCOC(C=C)OCC MCIPQLOKVXSHTD-UHFFFAOYSA-N 0.000 claims abstract description 4
- VVGOCOMZRGWHPI-ONEGZZNKSA-N (e)-hept-4-enal Chemical compound CC\C=C\CCC=O VVGOCOMZRGWHPI-ONEGZZNKSA-N 0.000 claims description 2
- VVGOCOMZRGWHPI-UHFFFAOYSA-N trans-hept-4-enal Natural products CCC=CCCC=O VVGOCOMZRGWHPI-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000003016 pheromone Substances 0.000 abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- VVGOCOMZRGWHPI-ARJAWSKDSA-N (z)-4-heptenal Chemical compound CC\C=C/CCC=O VVGOCOMZRGWHPI-ARJAWSKDSA-N 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 3
- 235000010254 Jasminum officinale Nutrition 0.000 abstract description 2
- 240000005385 Jasminum sambac Species 0.000 abstract description 2
- 244000246386 Mentha pulegium Species 0.000 abstract description 2
- 235000016257 Mentha pulegium Nutrition 0.000 abstract description 2
- 235000004357 Mentha x piperita Nutrition 0.000 abstract description 2
- 239000002413 animal pheromone Substances 0.000 abstract description 2
- 235000001050 hortel pimenta Nutrition 0.000 abstract description 2
- 239000000341 volatile oil Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000001747 exhibiting effect Effects 0.000 abstract 2
- CGDYZKZMGKZSMG-FPLPWBNLSA-N (z)-1,1-diethoxydec-7-en-4-ol Chemical compound CCOC(OCC)CCC(O)CC\C=C/CC CGDYZKZMGKZSMG-FPLPWBNLSA-N 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000004795 grignard reagents Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 4-propyl-5-oxo-cis-8- Undecenal Chemical compound 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NDFKTBCGKNOHPJ-AATRIKPKSA-N (E)-hept-2-enal Chemical compound CCCC\C=C\C=O NDFKTBCGKNOHPJ-AATRIKPKSA-N 0.000 description 1
- ZSSHTEYTRWOQKC-PLNGDYQASA-N 1-[(z)-hex-3-enyl]sulfonyl-4-methylbenzene Chemical compound CC\C=C/CCS(=O)(=O)C1=CC=C(C)C=C1 ZSSHTEYTRWOQKC-PLNGDYQASA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N caprinaldehyde Natural products CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- 229940090961 chromium dioxide Drugs 0.000 description 1
- IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 1
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- YWDLBBOFPKDNIJ-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O.CCCCCCCCCC=O YWDLBBOFPKDNIJ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- NDFKTBCGKNOHPJ-UHFFFAOYSA-N hex-2-enal Natural products CCCCC=CC=O NDFKTBCGKNOHPJ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LLUGFFSGUQULMF-UHFFFAOYSA-N nonadec-12-en-9-one Chemical compound CCCCCCCCC(=O)CCC=CCCCCCC LLUGFFSGUQULMF-UHFFFAOYSA-N 0.000 description 1
- AVHHVBVIOOAZHO-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O.CCCCCCCCC=O AVHHVBVIOOAZHO-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N pelargonaldehyde Natural products CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明はγ−ジャスモラクトンの製法に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to a method for producing γ-jasmolactone.
γ−ジャスモンラクトンはジャスミンあるいはペパーミ
ント等の精油から発見された香料として重要な物質であ
る。γ-Jasmonlactone is an important substance discovered from essential oils such as jasmine or peppermint as a fragrance.
（従来の技術）
従来、とのγ−ジャスモラクトンについては多くの製造
法が提案されている。これらの製造法の多くはグリニヤ
ール試薬を使用するものである。(Prior Art) Many production methods have been proposed for γ-jasmolactone. Many of these manufacturing methods use Grignard reagents.
例えば、グルタル酸無水物やフルフラールとグリニヤー
ル試薬との反応を含むγ−ジャスモラクトンの製法（ｉ
ｌｌｔ＋化学、Ｖｏｌ、２９．１９６頁（１９８０年）
）がある。For example, a method for producing γ-jasmolactone that involves the reaction of glutaric anhydride or furfural with a Grignard reagent (i
llt+chemistry, Vol. 29.196 pages (1980)
).
また、他の方法としては、１−（ｐ−トリルスルホニル
） −ｃ ｉ ｓ −３−ヘキセンを一７８℃でこはく
酸ジメチルと反応させる行程を経てγ−ジャスモラクト
ンを得る製法（Ｙｕｋａｇａｋｕ、 Ｖｏｌ、 ３２
。In addition, as another method, γ-jasmolactone is obtained through a step of reacting 1-(p-tolylsulfonyl)-cis-3-hexene with dimethyl succinate at -78°C (Yukagaku, Vol. , 32
.
８２頁（１９８３年））がある。82 pages (1983)).
（発明が解決しようとする問題点）
しかしながら従来のγ−ジャスモラクトンの製法は工程
が長いとか、グリニヤール試薬等の高価な試薬を用いる
とか、あるいは−７８℃のような過酷な反応条件が必要
となる等、いずれもγ−ジャスモラクトンの工業的製法
としては不適当なものであった。(Problems to be solved by the invention) However, conventional methods for producing γ-jasmolactone require long steps, use expensive reagents such as Grignard reagents, or require harsh reaction conditions such as -78°C. Both of these methods were unsuitable for industrial production of γ-jasmolactone.
本発明は上記した事情に鑑みてなされたものであり、簡
便なγ−ジャスモラクトンの製法を開発することを目的
としている。The present invention was made in view of the above-mentioned circumstances, and an object of the present invention is to develop a simple method for producing γ-jasmolactone.
（問題点を解決するための手段）
本発明者は上記した目的を達成するため、グリニヤール
試薬等の高価な試薬を用いることなく、かつ比較的温和
な反応条件下で得られる中間生成物、γ−オキソアルデ
ヒドアセタールを経る新規なジャスモン類の製法を見出
し本発明を完成した。(Means for Solving the Problems) In order to achieve the above-mentioned object, the present inventor has developed an intermediate product, γ, which can be obtained without using expensive reagents such as Grignard reagents and under relatively mild reaction conditions. - Discovered a new method for producing jasmones using oxoaldehyde acetal and completed the present invention.
本発明は、アクリルアルデヒドジエチルアセタールとシ
ス−４−ヘプテナールとのラジカル付加反応によりγ−
オキソアルデヒドアセタールを得、このものの還元生成
物である１、１−ジェトキシ−シス−７−デセン−４−
オールをジョーンズ試薬で酸化してγ−ジャスモラクト
ンを得ることを特徴としている。The present invention provides γ-
Oxoaldehyde acetal is obtained, and its reduction product 1,1-jethoxy-cis-7-decene-4-
It is characterized in that γ-jasmolactone is obtained by oxidizing ol with Jones reagent.
まス、アクリルアルデヒドジエチルアセタールとシス−
４−ヘプテナールとのラジカル付加反応によりγ−オキ
ソアルデヒドアセタールを製造する。Mas, acrylic aldehyde diethyl acetal and cis-
γ-oxoaldehyde acetal is produced by radical addition reaction with 4-heptenal.
ここで得られるγ−オキソアルデヒドアセタールは１．
１−ジェトキシ−シス−７−デセン−４−オンである。The γ-oxoaldehyde acetal obtained here is 1.
1-Jethoxy-cis-7-decen-4-one.
この工程では原料のアルデヒドの二重結合にアシルラジ
カルが付加した４−プロピル−５−オキソ−シス−８−
ウンデセナールや５−エチル−６−オキソ−シス−９−
ウンデセナールが副生成物としてできる。このため原料
に飽和アルデヒドを用いた場合よりも収率が若干低くな
る。In this step, 4-propyl-5-oxo-cis-8-
Undecenal and 5-ethyl-6-oxo-cis-9-
Undecenal is produced as a by-product. For this reason, the yield is slightly lower than when a saturated aldehyde is used as a raw material.
この中間生成物と同種のγ−オキソアルデヒドアセター
ルの中には動物のフェロモンとして活性を示すフェロモ
ン類の製造原料ともなる有用な物質を含み、このものも
同一の工程で製造できる。The γ-oxoaldehyde acetal, which is similar to this intermediate product, contains a substance useful as a raw material for producing pheromones that are active as animal pheromones, and can also be produced in the same process.
即ち、アクリルアルデヒドジエチルアセタールとノナナ
ール、デカナール、及びアセトアルデヒド等のアルデヒ
ドとのラジカル付加反応によりγ−オキソアルデヒドア
セタールを得、このものの加水分解生成物であるγ−オ
キソアルデヒドをウイッテヒ反応してそれぞれ、シス−
１２−ノナデセン−９−オン、シス−１３−エイコサン
−１０−オン、及びシス−５−ウンデセン−２−オンの
フェロモン類を得ることができる。That is, γ-oxoaldehyde acetal is obtained by a radical addition reaction of acrylicaldehyde diethyl acetal with aldehydes such as nonanal, decanal, and acetaldehyde, and γ-oxoaldehyde, which is a hydrolysis product of this acetal, is subjected to a Wittig reaction to form cis −
Pheromones of 12-nonadecen-9-one, cis-13-eicosan-10-one, and cis-5-undecen-2-one can be obtained.
次いで、前述した最初の工程で得たγ−オキソアルデヒ
ドアセタールを次工程で水素化はう素ナトリウムで還元
して１，１−ジェトキシ−シス−７−デセン−４−オー
ルを得る。次いでこのものをジョーンズ試薬で酸化して
γ−ジャスモラクトンを得る。The γ-oxoaldehyde acetal obtained in the first step described above is then reduced with sodium borohydride to obtain 1,1-jethoxy-cis-7-decen-4-ol. This is then oxidized with Jones's reagent to obtain γ-jasmolactone.
以下、本発明を実施例に基づいて具体的に説明する。Hereinafter, the present invention will be specifically explained based on Examples.
（実施例）
γ−オキソアルデヒドアセタールの製造還流冷却器、攪
拌機、滴下漏斗、温度計及び窒素ガス導入管を備えたフ
ラスコにシス−４−ヘプテナール０．２モルを入れ窒素
気流下、９０〜９５℃に加熱した。この中にシス−４−
ヘプテナール０．２モル、アクリルアルデヒドジエチル
アセタール０．１モル及び過酸化ベンゾイル４ミリモル
の混合物を３時間かけて滴下し、その後上記温度を保ち
ながら４時間攪拌を続けた。反応混合物を室温まで冷却
したのち、５％炭酸ナトリウム水溶液、及び飽和食塩水
で洗浄しな。油層を硫酸ナトリウム（無水物）で乾燥後
、減圧蒸留により１゜１−ジェトキシ−シス−７−デセ
ン−４−オンを得た。このときの収率は５１％であった
。(Example) Production of γ-oxoaldehyde acetal 0.2 mole of cis-4-heptenal was placed in a flask equipped with a reflux condenser, a stirrer, a dropping funnel, a thermometer, and a nitrogen gas introduction tube, and the temperature was increased to 90-90% under nitrogen flow. heated to ℃. In this, cis-4-
A mixture of 0.2 mol of heptenal, 0.1 mol of acrylic aldehyde diethyl acetal and 4 mmol of benzoyl peroxide was added dropwise over 3 hours, and then stirring was continued for 4 hours while maintaining the above temperature. After the reaction mixture was cooled to room temperature, it was washed with a 5% aqueous sodium carbonate solution and saturated brine. After drying the oil layer over sodium sulfate (anhydrous), 1.1-jetoxy-cis-7-decen-4-one was obtained by distillation under reduced pressure. The yield at this time was 51%.
１．１−ジェトキシ−シス−７−デセン−４−オールの
製造
還流冷却器、温度計、攪拌機及び滴下漏斗を備えたフラ
スコに１，１−ジェトキシ−シス−７−デセン−４−オ
ン０．０５モル、メタノール３０−を入れ、これに水素
化ホウ素ナトリウム０．０３モルのメタノール溶液２０
ｍ１を加えた。このものを室温で２時間攪拌した後、反
応混合物を２００−の飽和食塩水に注ぎ、エーテルで抽
出した。1. Preparation of 1-jetoxy-cis-7-decen-4-ol In a flask equipped with a reflux condenser, thermometer, stirrer and addition funnel, add 0.0% of 1,1-jethoxy-cis-7-decen-4-one. Add 0.05 mol of methanol and 30 mol of methanol, and add 0.03 mol of sodium borohydride methanol solution 20
m1 was added. After stirring the mixture at room temperature for 2 hours, the reaction mixture was poured into 200-saturated brine and extracted with ether.
抽出液を硫酸ナトリウム（無水物）で乾燥後、抽出溶媒
を留去し、残油を減圧蒸留して１，１−ジェトキシ−シ
ス−７−デセン−４−オールを得た。After drying the extract over sodium sulfate (anhydrous), the extraction solvent was distilled off, and the residual oil was distilled under reduced pressure to obtain 1,1-jethoxy-cis-7-decen-4-ol.
このときの収率は９０％であった。The yield at this time was 90%.
γ−ジャスモラクトンの製造
攪拌機、温度計及び滴下漏斗を備えたフラスコに１，１
−ジェトキシ−シス−７−デセン−４−オール０．０５
モル、７ セトン１００ ｍｊ’を入れ０℃に保った。Preparation of γ-jasmolactone In a flask equipped with a stirrer, a thermometer and a dropping funnel, add 1,1
-Jetoxy-cis-7-decen-4-ol 0.05
7 moles of setone and 100 mj' were added and kept at 0°C.
この中に二酸化クロム０．０４９モル、濃硫酸４．２ｇ
及び水２６ｍＺを用いて調整したジョーンズ試薬を０〜
５℃で反応液が橙色を呈するまで加え、その後３時間攪
拌を続けた。反応混合物を５００−の水に注ぎ、ジクロ
ロメタンで抽出した。抽出液を水で洗浄し、硫酸ナトリ
ウム（無水物）で乾燥した後、蒸留してγ−ジャスモラ
クトンを得た。このときの収率は８８％であった。This contains 0.049 mol of chromium dioxide and 4.2 g of concentrated sulfuric acid.
and Jones reagent prepared using water 26mZ from 0 to
The mixture was added at 5° C. until the reaction solution turned orange, and stirring was continued for 3 hours. The reaction mixture was poured into 500-ml water and extracted with dichloromethane. The extract was washed with water, dried over sodium sulfate (anhydrous), and then distilled to obtain γ-jasmolactone. The yield at this time was 88%.
（発明の効果）
以上、詳述したように本発明は、アクリルアルデヒドよ
り容易に得られるアクリルアルデヒドジエチルアセター
ルを原料とするものであるから原料の入手が容易である
とともに、反応工程中に動物のフェロモンとして活性を
示すフェロモン頚の製造原料ともなるγ−オキソアルデ
ヒドアセタールを製造できる工程を含むものであ−り有
用な製造法である。(Effects of the Invention) As detailed above, the present invention uses acrylaldehyde diethyl acetal, which can be easily obtained from acrylaldehyde, as a raw material, so the raw material is easy to obtain, and it does not require the use of animals during the reaction process. This is a useful manufacturing method as it includes a process for producing γ-oxoaldehyde acetal, which is also a raw material for producing pheromone necks that exhibit activity as pheromones.
また、本発明はグリニヤール試薬等の高価な試薬を用い
ることな（、かつ温和な反応条件で行うことができる等
の実用上の価値も著大である。Furthermore, the present invention has great practical value, as it does not require the use of expensive reagents such as Grignard reagents (and can be carried out under mild reaction conditions).
Claims (1)
４−ヘプテナールとのラジカル付加反応によりγ−オキ
ソアルデヒドアセタールを得、このものの還元生成物で
ある１，１−ジェトキシ−シス−７−デセン−４−オー
ルをジョーンズ試薬で酸化したことを特徴とするγ−ジ
ャスモラクトンの製法。(1) Acrylaldehyde diethyl acetal and cis-
It is characterized in that γ-oxoaldehyde acetal is obtained by a radical addition reaction with 4-heptenal, and 1,1-jethoxy-cis-7-decen-4-ol, which is a reduction product of this, is oxidized with Jones reagent. Method for producing γ-jasmolactone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26358686A JPS63119480A (en) | 1986-10-19 | 1986-11-05 | Production of gamma-jasmolactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26358686A JPS63119480A (en) | 1986-10-19 | 1986-11-05 | Production of gamma-jasmolactone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63119480A true JPS63119480A (en) | 1988-05-24 |
Family
ID=17391607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26358686A Pending JPS63119480A (en) | 1986-10-19 | 1986-11-05 | Production of gamma-jasmolactone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63119480A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112008002515T5 (en) | 2007-09-19 | 2010-07-15 | Toyota Jidosha Kabushiki Kaisha, Toyota-shi | Structure of a lateral vehicle body section |
-
1986
- 1986-11-05 JP JP26358686A patent/JPS63119480A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112008002515T5 (en) | 2007-09-19 | 2010-07-15 | Toyota Jidosha Kabushiki Kaisha, Toyota-shi | Structure of a lateral vehicle body section |
| US8308227B2 (en) | 2007-09-19 | 2012-11-13 | Toyota Jidoshi Kabushiki Kaisha | Structure for side portion of vehicle body |
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