JPS6141994B2 - - Google Patents
Info
- Publication number
- JPS6141994B2 JPS6141994B2 JP54077919A JP7791979A JPS6141994B2 JP S6141994 B2 JPS6141994 B2 JP S6141994B2 JP 54077919 A JP54077919 A JP 54077919A JP 7791979 A JP7791979 A JP 7791979A JP S6141994 B2 JPS6141994 B2 JP S6141994B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- citronellol
- reaction
- yield
- alkoxyoct
- 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
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 12
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 12
- 235000000484 citronellol Nutrition 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 238000000034 method Methods 0.000 description 11
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229930007790 rose oxide Natural products 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005868 electrolysis reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VKRQXMQEPSPVAG-UHFFFAOYSA-N 6-methoxy-3,7-dimethyloct-7-en-1-ol Chemical compound COC(C(C)=C)CCC(C)CCO VKRQXMQEPSPVAG-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 2
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QKFFSWPNFCXGIQ-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 QKFFSWPNFCXGIQ-UHFFFAOYSA-M 0.000 description 1
- CTENIPSAJGEQAA-UHFFFAOYSA-N 6-ethoxy-3,7-dimethyloct-7-en-1-ol Chemical compound CCOC(C(C)=C)CCC(C)CCO CTENIPSAJGEQAA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006198 methoxylation reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
本発明は２・６−ジメチル−３−アルコキシオ
クト−１−エン−８−オールの電気化学的製造方
法に関する。さらに詳しくは、シトロネロールを
陽極アルコキシ化するに際し、アルコール中に支
持塩として芳香族スルホン酸のアルカリ金属塩を
存在させることを特徴とする２・６−ジメチル−
３−アルコキシオクト−１−エン−８−オールの
製造方法である。
本発明方法によつて製造される２・６−ジメチ
ル−３−アルコキシオクト−１−エン−８−オー
ルは脱アルコールしてジエンアルコールとした
後、酸触媒を用いて閉環反応を行なえば高収率
で、ローズオキシドを生成する。ローズオキシド
は香料として有用な化学物質である。
シトロネロールの陽極メトキシ化に関しては、
Tetrahedron Letters、1971、3599にメタノール
中でｐ−トルエンスルホン酸の四級アルキルアン
モニウム塩を支持塩とし、電解を行う方法が記載
されている。この方法では、目的物２・６−ジメ
チル−３−メトキシオクト−１−エン−８−オー
ルの収率が低い上、取扱いが困難でかつ高温なｐ
−トルエンスルホン酸の四級アンモニウム塩を用
いる必要があり、これらの点において工業的製法
としては不満足なものである。
本発明者等は従来の方法の欠点を克服すること
に努めた結果、効果的かつ工業的に有利な２・６
−ジメチル−３−アルコキシオクト−１−エン−
８−オールの製造方法を見出した。
即ち、本発明は、シトロネロールを陽極アルコ
キシ化するに際し、アルコール中に支持塩とし
て、芳香族スルホン酸のアルカリ金属塩を存在さ
せることにより収率良く、２・６−ジメチル−３
−アルコキシオクト−１−エン−８−オールを製
造する方法を提供する。
本発明方法で用いる芳香族スルホン酸のアルカ
リ金属塩は、製造、取扱いが容易であるばかりで
なく、回収、再使用も可能であり、従来の支持塩
に比べて工業的電解の実施上、大きな利点があ
る。
本発明における陽極アルコキシ化は、電解反応
の常法に従つて行われるが、溶媒兼反応試剤のア
ルコールとしては、C1ないしC3の低級アルコー
ルが用いられる。中でもメタノールが特に好適で
ある。
支持塩としては、一般の芳香族スルホン酸アル
カリ金属塩を用いることができるが、特に芳香族
基として低級アルキル置換または無置換ベンゼン
核を有するものが好ましい。また、アルカリ金属
の種類としてナトリウム、カリウムを有するもの
が好ましい。
優れた支持塩の具体例として、ベンゼンスルホ
ン酸ナトリウム、ｐ−トルエンスルホン酸ナトリ
ウム、ナフタレンスルホン酸ナトリウム等が挙げ
られる。
これらの支持塩の電解液中濃度の好ましい範囲
は0.5ないし10重量％、更に好ましくは１ないし
３重量％である。
原料シトロネロールの電解液中濃度は特に限定
されないが、低濃度では不経済であり、またあま
りに高濃度では目的物収率の低下を招き不利であ
る。５ないし60重量％、好ましくは10ないし40重
量％の範囲が適当である。なお、原料に光学活性
のシトロネロールを使用すれば生成物は光学活性
の化合物が得られる。
本発明方法に従つて電解を行なう場合、陽極と
しては炭素、白金等の材料が用いられるが、特に
炭素が好ましい。た陰極としては、炭素、黒鉛の
他に白金、アルミニウム、銀、銅、鋼等の金属あ
るいは合金が用いられる。
電解槽は隔膜等で分割された電槽および分割さ
れない電槽のいずれを用いても良い。
このような電槽内で電解を実施する際、電極間
電位を２ないし10ボルトの範囲に、電流密度を
0.5ないし20A/dm2の範囲に保つことが好まし
い。電解液の温度はアルコールの沸点以下であれ
ば特に制限がないが、40℃以上が好ましい結果を
与える。
本発明方法によつて製造される２・６−ジメチ
ル−３−アルコキシオクト−１−エン−８−オー
ルは蒸留、抽出等を組み合わせた通常の処理によ
つて分離ならびに精製して取得される。
未反応の原料シトロネロール、支持塩及びアル
コールは、蒸留、抽出等の手段によつて分離回収
した後、再び電解反応に使用できる。
本発明をより効果的に実施するためには陽極液
を激しく撹拌することが望ましいが、これは通常
のかきまぜ棒による撹拌あるいはポンプによる高
速循環等の手段により容易に達成できる。
以下、本発明の具体的方法を実施例で説明す
る。
生成物の同定および定量はIR.NMR.ガスクロ
マトグラフイー法および質量分析法によつた。
ここで、収率は以下の式の値を意味する。
電解生成物のモル数／原料シトロネロールのモル数×
100（％）
実施例 １
内容積30c.c.のガラス製容器に電極として径10
mm、長さ30mmの炭素棒２本を挿入し両極の間隔を
２mmに保ち固定した。この電槽にメタノール11
ｇ、シトロネロール1.2ｇ、ベンゼンスルホン酸
ナトリウム0.2ｇを加えた後室温で窒素下、定電
流0.25AでＦ／ｍ＝3.0に達するまで電解を行なつ
た。
この間、極間電圧を４ないし５ボルトに保つ
た。
反応液の分析結果は以下の通りであつた。
シトロネロール反応率 94.6％
２・６−ジメチル−３−メトキシオクト−１−
エン−８−オール（少量の位置異性体を含む）
収率 56.4％
２・６−ジメチル−２・３−ジメトキシオクタ
ノール−８収率 9.5％
ローズオキシド収率 2.7％
実施例 ２〜４
支持塩を変えた以外は実施例１と同様な方法で
反応を行なつた。但し、実施例４では、反応液の
温度を60℃とした。
結果は表１に示す。
The present invention relates to an electrochemical method for producing 2,6-dimethyl-3-alkoxyoct-1-en-8-ol. More specifically, when citronellol is anodic alkoxylated, a 2,6-dimethyl-
This is a method for producing 3-alkoxyoct-1-en-8-ol. 2,6-dimethyl-3-alkoxyoct-1-en-8-ol produced by the method of the present invention can be dealcoholized to diene alcohol and then subjected to a ring-closing reaction using an acid catalyst to obtain a high yield. produces rose oxide at a high rate. Rose oxide is a chemical useful as a fragrance. Regarding the anodic methoxylation of citronellol,
Tetrahedron Letters, 1971, 3599 describes a method of electrolyzing in methanol using a quaternary alkyl ammonium salt of p-toluenesulfonic acid as a supporting salt. In this method, the yield of the target product 2,6-dimethyl-3-methoxyoct-1-en-8-ol is low, and it is difficult to handle and requires high temperature plating.
- It is necessary to use a quaternary ammonium salt of toluenesulfonic acid, and in these respects it is unsatisfactory as an industrial production method. The present inventors have endeavored to overcome the shortcomings of the conventional methods, and as a result, we have developed an effective and industrially advantageous 2.6 method.
-dimethyl-3-alkoxyoct-1-ene-
We have discovered a method for producing 8-ol. That is, in the present invention, when citronellol is anodic alkoxylated, 2,6-dimethyl-3
A method for producing -alkoxyoct-1-en-8-ol is provided. The alkali metal salt of aromatic sulfonic acid used in the method of the present invention is not only easy to produce and handle, but also recoverable and reusable, making it more suitable for industrial electrolysis than conventional supporting salts. There are advantages. The anodic alkoxylation in the present invention is carried out according to a conventional electrolytic reaction method, and a C 1 to C 3 lower alcohol is used as the alcohol serving as a solvent and reaction reagent. Among them, methanol is particularly suitable. As the supporting salt, general alkali metal salts of aromatic sulfonic acids can be used, but those having a lower alkyl-substituted or unsubstituted benzene nucleus as the aromatic group are particularly preferred. Moreover, those having sodium and potassium as the alkali metal types are preferable. Specific examples of excellent supporting salts include sodium benzenesulfonate, sodium p-toluenesulfonate, sodium naphthalenesulfonate, and the like. The preferred concentration range of these supporting salts in the electrolyte is 0.5 to 10% by weight, more preferably 1 to 3% by weight. The concentration of raw material citronellol in the electrolyte is not particularly limited, but a low concentration is uneconomical, and an excessively high concentration is disadvantageous as it leads to a decrease in the yield of the target product. A range of 5 to 60% by weight, preferably 10 to 40% by weight is suitable. Note that if optically active citronellol is used as a raw material, an optically active compound can be obtained as a product. When performing electrolysis according to the method of the present invention, materials such as carbon and platinum are used as the anode, with carbon being particularly preferred. In addition to carbon and graphite, metals or alloys such as platinum, aluminum, silver, copper, and steel are used as the cathode. The electrolytic cell may be either a cell divided by a diaphragm or the like, or a cell not divided. When performing electrolysis in such a tank, the potential between the electrodes should be in the range of 2 to 10 volts, and the current density should be in the range of 2 to 10 volts.
It is preferable to keep it within the range of 0.5 to 20 A/dm 2 . The temperature of the electrolytic solution is not particularly limited as long as it is below the boiling point of alcohol, but a temperature of 40°C or above gives preferable results. The 2,6-dimethyl-3-alkoxyoct-1-en-8-ol produced by the method of the present invention is obtained by separating and purifying it by a conventional process combining distillation, extraction, etc. The unreacted raw material citronellol, supporting salt, and alcohol can be separated and recovered by means such as distillation and extraction, and then used again in the electrolytic reaction. In order to carry out the present invention more effectively, it is desirable to vigorously stir the anolyte, and this can be easily achieved by means such as stirring with a conventional stir bar or high-speed circulation using a pump. Hereinafter, specific methods of the present invention will be explained using Examples. Identification and quantification of the product was performed using IR, NMR, gas chromatography and mass spectrometry. Here, the yield means the value of the following formula. Number of moles of electrolyzed product / number of moles of raw material citronellol ×
100 (%) Example 1 A glass container with an internal volume of 30 c.c. has a diameter of 10 mm as an electrode.
Two carbon rods with a length of 30 mm and a length of 30 mm were inserted and fixed with a distance of 2 mm between the poles. Methanol 11 in this tank
After adding 1.2 g of citronellol and 0.2 g of sodium benzenesulfonate, electrolysis was carried out at room temperature under nitrogen at a constant current of 0.25 A until F/m=3.0. During this time, the interelectrode voltage was maintained at 4 to 5 volts. The analysis results of the reaction solution were as follows. Citronellol reaction rate 94.6% 2,6-dimethyl-3-methoxyoct-1-
En-8-ol (contains small amounts of positional isomers)
Yield 56.4% 2,6-dimethyl-2,3-dimethoxyoctanol-8 Yield 9.5% Rose oxide yield 2.7% Examples 2 to 4 The reaction was carried out in the same manner as in Example 1 except that the supporting salt was changed. I did it. However, in Example 4, the temperature of the reaction solution was 60°C. The results are shown in Table 1.
【表】
実施例 ５
メタノールをエタノールに、反応温度を60℃に
変えた以外は実施例１と同様な方法で反応を行な
つた。
反応中、極間電圧を７ないし８ボルトに保つ
た。
反応液の分析結果は以下の通りであつた。
シトロネロール反応率 84.9％
２・６−ジメチル−３−エトキシオクト−１−
エン−８−オール（少量の位置異性体を含む）
収率 44.3％
ローズオキシド収率 2.0％
比較例 １
支持塩としてｐ−トルエンスルホン酸テトラエ
チルアンモニウム0.3ｇ（１ミリモル）を用いた
以外は実施例１と同様の方法で反応を行なつた。
反応液の分析結果は以下の通りであつた。
シトロネロール反応率 96.8％
２・６−ジメチル−３−メトキシオクト−１−
エン−８−オール（少量の異性体を含む）収率
33.5％
２・６−ジメチル−２・３−ジメトキシオクタ
ノール−８収率 8.3％
ローズオキシド収率 4.0％[Table] Example 5 A reaction was carried out in the same manner as in Example 1 except that methanol was replaced with ethanol and the reaction temperature was changed to 60°C. The interelectrode voltage was maintained at 7 to 8 volts during the reaction. The analysis results of the reaction solution were as follows. Citronellol reaction rate 84.9% 2,6-dimethyl-3-ethoxyoct-1-
En-8-ol (contains small amounts of positional isomers)
Yield: 44.3% Rose oxide yield: 2.0% Comparative Example 1 The reaction was carried out in the same manner as in Example 1, except that 0.3 g (1 mmol) of tetraethylammonium p-toluenesulfonate was used as the supporting salt. The analysis results of the reaction solution were as follows. Citronellol reaction rate 96.8% 2,6-dimethyl-3-methoxyoct-1-
En-8-ol (contains minor isomers) yield
33.5% 2,6-dimethyl-2,3-dimethoxyoctanol-8 Yield 8.3% Rose oxide yield 4.0%
Claims (1)
し、アルコール中で支持塩として、芳香族スルホ
ン酸のアルカリ金属塩を存在させることを特徴と
する２・６−ジメチル−３−アルコキシオクト−
１−エン−８−オールの製造方法。 ２ アルコールがメタノールである特許請求の範
囲第１項記載の２・６−ジメチル−３−アルコキ
シオクト−１−エン−８−オールの製造方法。 ３ 電解反応液温度が40℃以上である特許請求の
範囲第１項記載の２・６−ジメチル−３−アルコ
キシオクト−１−エン−８−オールの製造方法。[Scope of Claims] 1. 2,6-dimethyl-3-alkoxyocto-, which is characterized in that an alkali metal salt of an aromatic sulfonic acid is present as a supporting salt in an alcohol when citronellol is anodic alkoxylated.
Method for producing 1-en-8-ol. 2. The method for producing 2,6-dimethyl-3-alkoxyoct-1-en-8-ol according to claim 1, wherein the alcohol is methanol. 3. The method for producing 2,6-dimethyl-3-alkoxyoct-1-en-8-ol according to claim 1, wherein the electrolytic reaction solution temperature is 40°C or higher.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7791979A JPS563687A (en) | 1979-06-19 | 1979-06-19 | Manufacture of 2,6-dimethyl-3-alkoxyoct-1-en-8-ol |
| US06/158,810 US4312717A (en) | 1979-06-19 | 1980-06-12 | Process for producing 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| EP80302027A EP0021769B1 (en) | 1979-06-19 | 1980-06-16 | Processes for producing 2,6-dimethyl-3-alkoxy-oct-1-en-8-ol, dehydrocitronellol and 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| DE8080302027T DE3062269D1 (en) | 1979-06-19 | 1980-06-16 | Processes for producing 2,6-dimethyl-3-alkoxy-oct-1-en-8-ol, dehydrocitronellol and 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
| US06/289,071 US4340544A (en) | 1979-06-19 | 1981-07-31 | Process for producing 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7791979A JPS563687A (en) | 1979-06-19 | 1979-06-19 | Manufacture of 2,6-dimethyl-3-alkoxyoct-1-en-8-ol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS563687A JPS563687A (en) | 1981-01-14 |
| JPS6141994B2 true JPS6141994B2 (en) | 1986-09-18 |
Family
ID=13647478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7791979A Granted JPS563687A (en) | 1979-06-19 | 1979-06-19 | Manufacture of 2,6-dimethyl-3-alkoxyoct-1-en-8-ol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS563687A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5938392A (en) * | 1982-08-26 | 1984-03-02 | Sumitomo Chem Co Ltd | Manufacture of 2-propargyl-3-methyl-4-hydroxy-2- cyclopentenone |
-
1979
- 1979-06-19 JP JP7791979A patent/JPS563687A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS563687A (en) | 1981-01-14 |
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