JPS6354333A - Optically active alcohol compound - Google Patents
Optically active alcohol compoundInfo
- Publication number
- JPS6354333A JPS6354333A JP19678886A JP19678886A JPS6354333A JP S6354333 A JPS6354333 A JP S6354333A JP 19678886 A JP19678886 A JP 19678886A JP 19678886 A JP19678886 A JP 19678886A JP S6354333 A JPS6354333 A JP S6354333A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- compound
- formula
- alcohol compound
- methyl
- 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
- -1 alcohol compound Chemical class 0.000 title claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007818 Grignard reagent Substances 0.000 abstract description 4
- 150000004795 grignard reagents Chemical class 0.000 abstract description 4
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 4
- 238000011914 asymmetric synthesis Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000002140 halogenating effect Effects 0.000 abstract description 2
- 230000001766 physiological effect Effects 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZPMNDFWZBJOEEO-UHFFFAOYSA-N 6-methyldecan-1-ol Chemical compound CCCCC(C)CCCCCO ZPMNDFWZBJOEEO-UHFFFAOYSA-N 0.000 description 4
- SIYMPAJYSQLNOH-UHFFFAOYSA-N 6-methylundecan-1-ol Chemical compound CCCCCC(C)CCCCCO SIYMPAJYSQLNOH-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PZZBSMKSCWYJJW-UHFFFAOYSA-N 1-bromo-3-methyloctane Chemical compound CCCCCC(C)CCBr PZZBSMKSCWYJJW-UHFFFAOYSA-N 0.000 description 2
- GTVXMPDPXBTLCQ-UHFFFAOYSA-N 6-methylnonan-1-ol Chemical compound CCCC(C)CCCCCO GTVXMPDPXBTLCQ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000005968 1-Decanol Substances 0.000 description 1
- MRLAKDCGXYAZCI-UHFFFAOYSA-N 1-bromo-4-methylheptane Chemical compound CCCC(C)CCCBr MRLAKDCGXYAZCI-UHFFFAOYSA-N 0.000 description 1
- FNMGIYBVDJJRHV-UHFFFAOYSA-N 6-methyldodecan-1-ol Chemical compound CCCCCCC(C)CCCCCO FNMGIYBVDJJRHV-UHFFFAOYSA-N 0.000 description 1
- QITMGEIDLGSWJI-UHFFFAOYSA-N 6-methylpentadecan-1-ol Chemical compound CCCCCCCCCC(C)CCCCCO QITMGEIDLGSWJI-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は特定の光学活性アルコール化合物に関し、詳し
くは、不斉炭素を有する６−メチル−１−アルカノール
化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a specific optically active alcohol compound, and more particularly to a 6-methyl-1-alkanol compound having an asymmetric carbon.
メチル分岐を有するアルコール化合物は、化粧品、医薬
の中間原料等の種々の工業薬品として有用であり、特に
、光学活性アルコール化合物は、液晶化学物質用中間体
として近年特に注目を集めている０例えば、アルコキシ
フェニルピリミジン化合物、アルコキシ安息香酸誘導体
等は強誘電性スメクチック液晶化学物質として知られて
いる。Alcohol compounds having a methyl branch are useful as various industrial chemicals such as intermediate raw materials for cosmetics and pharmaceuticals.In particular, optically active alcohol compounds have attracted particular attention in recent years as intermediates for liquid crystal chemicals. Alkoxyphenylpyrimidine compounds, alkoxybenzoic acid derivatives, and the like are known as ferroelectric smectic liquid crystal chemicals.
これらの液晶化合物におけるアルコキシ基としては、２
−メチルブトキシあるいは６−メチルオクトキシ等の比
較的炭素数の小さいアルコールから誘導されるアルコキ
シ基が知られているが、これらの化合物は使用可能温度
範囲が適切でなかったり、あるいは安定性が劣ったりす
る問題を有しており、実用上満足しえるものではなかっ
た。The alkoxy group in these liquid crystal compounds is 2
- Alkoxy groups derived from alcohols with relatively small carbon numbers such as methylbutoxy or 6-methyloctoxy are known, but these compounds do not have an appropriate usable temperature range or have poor stability. However, it was not practically satisfactory.
このため、より炭素数の多い光学活性アルコールが求め
られていた。For this reason, optically active alcohols with a larger number of carbon atoms have been sought.
本発明者等は、６位にメチル分岐を有するアルコール化
合物について検討を重ねた結果、次の一般式（Ｉ）で表
される化合物が優れた光学活性を有していることを見出
した。As a result of repeated studies on alcohol compounds having a methyl branch at the 6-position, the present inventors found that a compound represented by the following general formula (I) has excellent optical activity.
ＨＯ（ＣＨｚ）ｓ ＣＨ−Ｒ（Ｉ）
ＣＨ３
（式中、Ｒは炭素原子数３〜９の直鎖アルキル基を示し
、＊は不斉炭素を示す。）
本発明の光学活性アルコールは、工業薬品として重要な
物質である０例えば、上記の液晶化合物用の中間体以外
にも、光学分割剤あるいは不斉合成の助剤として有用で
あり、また種々の生理活性も期待される。HO(CHz)s CH-R(I) CH3 (In the formula, R represents a straight-chain alkyl group having 3 to 9 carbon atoms, and * represents an asymmetric carbon.) In addition to being an important substance as a drug, for example, as an intermediate for the above-mentioned liquid crystal compounds, it is also useful as an optical resolution agent or an aid for asymmetric synthesis, and is also expected to have various physiological activities.
以下本発明について更に詳細に説明する。The present invention will be explained in more detail below.
Ｒで示されるアルキル基としては、プロピル、ブチル、
ペンチル、ヘキシル、ヘプチル、オクチル及びノニル基
があげられる。The alkyl group represented by R includes propyl, butyl,
Mention may be made of pentyl, hexyl, heptyl, octyl and nonyl groups.
上記一般式（Ｉ）で表される化合物としては、６−メチ
ルノナノール、６−メチルデカノール、６−メチルウン
デカノール、６−メチルドデカノール、６−メチルウン
デカノール、６−メチルウンデカノール、６−メチルペ
ンタデカノールがあげられる。Examples of the compound represented by the above general formula (I) include 6-methylnonanol, 6-methyldecanol, 6-methylundecanol, 6-methyldodecanol, 6-methylundecanol, 6-methylundecanol, and 6-methylundecanol. Examples include decanol and 6-methylpentadecanol.
これらの化合物は、例えば、光学活性の４−メチルアル
カノール化合物をハロゲン化し、これからグリニヤール
試薬を作成し、エチレンオキサイドを反応させることに
より製造することができる。These compounds can be produced, for example, by halogenating an optically active 4-methylalkanol compound, preparing a Grignard reagent therefrom, and reacting it with ethylene oxide.
次に、本発明を実施例によって説明する。しかし、本発
明はこれらの実施例によって制限されるものではない。Next, the present invention will be explained by examples. However, the present invention is not limited to these examples.
実施例１
６−メチル−１−ノナノー１＋／（７）合成光学活性な
４−メチルヘプタツール６５．０ｇを攪拌しながら、室
温で、濃硫酸２５．０ｇと４７％臭化水素酸１２７．０
ｇを交互にゆっくりと滴下した。次いで混合物を５時
間還流下に攪拌した。Example 1 Synthesis of 6-methyl-1-nonano 1+/(7) While stirring 65.0 g of optically active 4-methylheptatool, 25.0 g of concentrated sulfuric acid and 127.0 g of 47% hydrobromic acid were mixed at room temperature.
g was slowly added dropwise alternately. The mixture was then stirred under reflux for 5 hours.
反応生成物を水蒸気蒸溜し、混合物から分離した後、有
機層を濃硫酸２０ ｍｌ、メタノール／水混合溶液（Ｉ
／９）４０ｍｌ、飽和重炭酸ソーダ水溶液４００１１及
び水４０＋ｎｌで各２回ずつ洗浄した後、塩化カルシウ
ムで乾燥した。After the reaction product was separated from the mixture by steam distillation, the organic layer was dissolved in 20 ml of concentrated sulfuric acid and a methanol/water mixed solution (I
/9) After washing twice each with 40 ml of saturated aqueous sodium bicarbonate solution 40011 and 40+ nl of water, it was dried over calcium chloride.
減圧下に蒸溜し、７２．８ｇ （収率７５％）の４−メ
チルヘプチルブロマイド（沸点５４〜５６℃／１０ｍｍ
Ｈｇ）を得た。Distilled under reduced pressure to obtain 72.8g (yield 75%) of 4-methylheptyl bromide (boiling point 54-56℃/10mm
Hg) was obtained.
４−メチルへブチルブロマイド５２．８ ｇ 、金属マ
グネシウム８．０ｇ及びジエチルエーテル３００ｍ１よ
り、グリニヤール試薬を調製し、５〜１０℃でゆっくり
エチレンオキシド１５．８ｇを加えた。次いで、ｘ−−
フルロ０ｍｌを溜去し、ベンゼン１５０ｍ１を加え、温
度が６５℃に達するまで更に蒸溜を続けた。A Grignard reagent was prepared from 52.8 g of 4-methylhebutyl bromide, 8.0 g of metallic magnesium, and 300 ml of diethyl ether, and 15.8 g of ethylene oxide was slowly added at 5 to 10°C. Then x--
0 ml of Fluoro was distilled off, 150 ml of benzene was added, and further distillation was continued until the temperature reached 65°C.
この混合物を１時間還流させた後、１０％硫酸で加水分
解し、ベンゼン層を分離した。ベンゼン層を１０％苛性
ソーダ水溶液２００＋ｌ ｌで２回、水２０抛１で３回
洗浄し、芒硝で乾燥し、脱溶媒、蒸溜して沸点１１９〜
１２０℃／４０ ｍｄｇの６−メチル−１−ノナノール
５２．９ ｇ （収率６５％）を得た。The mixture was refluxed for 1 hour, then hydrolyzed with 10% sulfuric acid, and the benzene layer was separated. The benzene layer was washed twice with 200 liters of 10% aqueous sodium hydroxide solution and three times with 20 liters of water, dried with Glauber's salt, removed the solvent, and distilled to a boiling point of 119~1.
52.9 g (yield 65%) of 6-methyl-1-nonanol was obtained at 120°C/40 mdg.
目的物の一部をシリカゲルカラムで精製（ヘキサン／酢
酸エチル＝８／２）Ｌ、更にクーゲルロールで蒸溜した
後、比旋光度を測定した。A portion of the target product was purified using a silica gel column (hexane/ethyl acetate = 8/2) and further distilled using a Kugelrohr, and then the specific optical rotation was measured.
〔α〕。＝＋１．６７” （２８℃、１．４３２％ク
ロロホルム溶液）
実施例２
６−メチル−１−デカノールの人
〔α〕。＝−１，４１° （２７℃、１．９７２％クロ
ロホルム溶液）の３−メチル−１−オクタツール１０１
．６ｇ（純度９７．６％）を５００ｍ Ｉフラスコに取
り、濃硫酸５０．６ｇ及び４７％臭化水素酸２６６．３
ｇを１時間を要して滴下した。還流下４時間反応させ
た後、濃硫酸１６．９ ｇ及び４７％臭化水素酸８８．
８ｇを追加し、更に２時間還流下に反応させた。[α]. = +1.67" (28°C, 1.432% chloroform solution) Example 2 6-methyl-1-decanol [α]. = -1,41° (27°C, 1.972% chloroform solution) 3-methyl-1-octatool 101
．． 6g (purity 97.6%) was placed in a 500m I flask and added with 50.6g of concentrated sulfuric acid and 266.3g of 47% hydrobromic acid.
g was added dropwise over a period of 1 hour. After 4 hours of reaction under reflux, 16.9 g of concentrated sulfuric acid and 88.9 g of 47% hydrobromic acid were added.
8 g was added and the reaction was further continued under reflux for 2 hours.
反応混合物を水蒸気蒸溜し、約１３９ｇの微黄色油状の
生成物を得た。これを５０ｍ１の濃硫酸で２回、１００
ｍ１の１０％苛性ソーダ水溶液で２回、１００ ｍｌの
１０％重炭酸ソーダ水溶液で２回洗浄した後、更に飽和
食塩水で洗浄し、無水芒硝で乾燥し、脱溶媒を行った。The reaction mixture was steam distilled to obtain about 139 g of a slightly yellow oily product. This was washed twice with 50ml of concentrated sulfuric acid for 100ml.
After washing twice with 100 ml of 10% aqueous sodium hydroxide solution and twice with 100 ml of 10% aqueous sodium bicarbonate solution, it was further washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was removed.
純度９８．４％（ガスクロマトグラフィー）の３−メチ
ル−１−オクチルブロマイド１３３．６ｇを得た。133.6 g of 3-methyl-1-octyl bromide with a purity of 98.4% (gas chromatography) was obtained.
次いで、アルゴン雰囲気下で、４８ｍ ｌの無水エーテ
ルに分散させた１６．２ ｇ （０，６６７モル）の金
属マグネシウムに、４００ ｍｌの無水エーテルに溶解
した上記３−メチル−１−オクチルブロマイド１３３．
６ ｇ（０，６３５モル）を滴下し、グリニヤール試薬
を調製した。この溶液を−５〜−１０℃に冷却しながら
、３３．６ ｇ （０，７６２モル）のエチレンオキサ
イドを滴下した０滴下終了後冷媒を取り除くと、穏やか
な発熱により還流が始まるので、発熱がなくなるまで約
２時間反応させた。Then, under an argon atmosphere, 16.2 g (0,667 mol) of metallic magnesium dispersed in 48 ml of anhydrous ether were treated with 133.1 g of the above 3-methyl-1-octyl bromide dissolved in 400 ml of anhydrous ether.
6 g (0,635 mol) was added dropwise to prepare a Grignard reagent. While cooling this solution to -5 to -10°C, 33.6 g (0,762 mol) of ethylene oxide was added dropwise. After the completion of the dropwise addition, the refrigerant was removed, and reflux started with a mild exotherm. The reaction was continued for about 2 hours until the solution disappeared.
３５０ ｍｌの乾燥ベンゼンを加え、還流冷却器を蛇管
冷却器に換え、エーテル約５００ｍ ｌを溜去させ、６
５℃とし、１時間保持した。その後反応混合物を０℃ま
で冷却し、３００ ｍｌの氷水で加水分解させ、更に３
０％硫酸水溶液５００ｍ１を加え、沈澱物を完全に溶解
させた。油層を分離し、１０％苛性ソーダ水溶液、飽和
食塩水で洗浄し、乾燥、脱溶媒をすることにより、ガス
クロマトグラフィーによる純度８５．２％の６−メチル
−１−デカノール１０５．４ｇを得た。これを減圧下に
蒸溜し、純度９４．０％の６−メチル−１−デカノール
７０．０ｇを得た。これを更にクーゲルロールで精留し
、シリカゲルを用い、ヘキサン／酢酸エチル（８／２）
展開溶媒により精製し、純度９９．８％の６−メチル−
１−デカノールを得た。（沸点７７℃／ ｌ ａｍ）Ｉ
ｇ）旋光度及びＩＲを測定した。Add 350 ml of dry benzene, replace the reflux condenser with a condenser condenser, and distill off about 500 ml of ether.
The temperature was kept at 5°C for 1 hour. The reaction mixture was then cooled to 0°C, hydrolyzed with 300 ml of ice water, and further
500 ml of 0% sulfuric acid aqueous solution was added to completely dissolve the precipitate. The oil layer was separated, washed with a 10% aqueous sodium hydroxide solution and saturated brine, dried, and removed to obtain 105.4 g of 6-methyl-1-decanol with a purity of 85.2% as determined by gas chromatography. This was distilled under reduced pressure to obtain 70.0 g of 6-methyl-1-decanol with a purity of 94.0%. This was further rectified with a Kugelrohr, and using silica gel, hexane/ethyl acetate (8/2) was used.
6-Methyl-purified with a developing solvent and has a purity of 99.8%.
1-Decanol was obtained. (boiling point 77℃/l am)I
g) Optical rotation and IR were measured.
〔α〕。＝−０，６２＠（２７℃、１．６１２％クロロ
ホルム溶液）
Ｉ Ｒ： ３３４０．２９５０．２８６０．１４６０．
１３８０．１０６０．７３０ ｃｍ−’[α]. =-0,62@(27°C, 1.612% chloroform solution) I R: 3340.2950.2860.1460.
1380.1060.730 cm-'
Claims (1)
物 ▲数式、化学式、表等があります▼（ I ） （式中、Ｒは炭素原子数３〜９の直鎖アルキル基を示し
、＊は不斉炭素を示す。）[Claims] An optically active alcohol compound represented by the following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) (In the formula, R is a straight chain alkyl having 3 to 9 carbon atoms. group, and * indicates an asymmetric carbon.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19678886A JPS6354333A (en) | 1986-08-22 | 1986-08-22 | Optically active alcohol compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19678886A JPS6354333A (en) | 1986-08-22 | 1986-08-22 | Optically active alcohol compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6354333A true JPS6354333A (en) | 1988-03-08 |
Family
ID=16363652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19678886A Pending JPS6354333A (en) | 1986-08-22 | 1986-08-22 | Optically active alcohol compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6354333A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116813A (en) * | 1989-03-15 | 1992-05-26 | Kao Corporation | Perfume composition |
| US5365691A (en) * | 1992-08-24 | 1994-11-22 | Bayer Aktiengesellschaft | Methods and agents for combating cockroaches |
| US5843510A (en) * | 1995-05-02 | 1998-12-01 | Rheon Automatic Machinery Co., Ltd. | Method for stretching bread dough and the like |
| US7205017B2 (en) | 2002-09-03 | 2007-04-17 | Rheon Automatic Machinery Co., Ltd. | Apparatus and method for beating and rolling a food dough belt |
-
1986
- 1986-08-22 JP JP19678886A patent/JPS6354333A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116813A (en) * | 1989-03-15 | 1992-05-26 | Kao Corporation | Perfume composition |
| US5365691A (en) * | 1992-08-24 | 1994-11-22 | Bayer Aktiengesellschaft | Methods and agents for combating cockroaches |
| US5843510A (en) * | 1995-05-02 | 1998-12-01 | Rheon Automatic Machinery Co., Ltd. | Method for stretching bread dough and the like |
| US7205017B2 (en) | 2002-09-03 | 2007-04-17 | Rheon Automatic Machinery Co., Ltd. | Apparatus and method for beating and rolling a food dough belt |
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