JP3357570B2 - Method for producing 3-substituted-1-propanol - Google Patents
Method for producing 3-substituted-1-propanolInfo
- Publication number
- JP3357570B2 JP3357570B2 JP13058097A JP13058097A JP3357570B2 JP 3357570 B2 JP3357570 B2 JP 3357570B2 JP 13058097 A JP13058097 A JP 13058097A JP 13058097 A JP13058097 A JP 13058097A JP 3357570 B2 JP3357570 B2 JP 3357570B2
- Authority
- JP
- Japan
- Prior art keywords
- propanol
- propylamine
- acid
- substituted
- diazonium salt
- 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 - Lifetime
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Description
【０００１】[0001]
【発明の属する技術分野】本発明は、３−置換−１−プ
ロパノールの製造方法に関する。さらに詳しくは、３−
アルコキシ（又は３−アルキルチオ）−１−プロピルア
ミンを亜硝酸類と反応させ、得られたジアゾニウム塩を
分解することを特徴とする３−アルコキシ（又は３−ア
ルキルチオ）−１−プロパノールの製造方法に関する。[0001] The present invention relates to a method for producing 3-substituted-1-propanol. For more details, see 3-
The present invention relates to a method for producing 3-alkoxy (or 3-alkylthio) -1-propanol, which comprises reacting alkoxy (or 3-alkylthio) -1-propylamine with nitrous acid to decompose the resulting diazonium salt. .
【０００２】[0002]
【従来の技術】従来、３−アルコキシ−１−プロパノー
ルの製造方法としては、アルコール中で３−クロロ−１
−プロパノールをアルカリ金属アルコキシドと反応させ
て、３−アルコキシ−１−プロパノールを得る方法（特
開平８−１１３５４６号公報）、及び１，３−プロパン
ジオールと金属ナトリウムから得られるアルコキシド
と、ハロゲン化アルキルとを反応させて、３−アルコキ
シ−１−プロパノールを得る方法（J. Am. Chem. Soc.,
65 (1943), 1276）が知られている。2. Description of the Related Art Conventionally, a method for producing 3-alkoxy-1-propanol has been to prepare 3-chloro-1-propanol in alcohol.
-Propanol reacting with an alkali metal alkoxide to give 3-alkoxy-1-propanol (JP-A-8-113546), and an alkoxide obtained from 1,3-propanediol and metal sodium, and an alkyl halide To obtain 3-alkoxy-1-propanol (J. Am. Chem. Soc.,
65 (1943), 1276).
【０００３】また、３−アルキルチオ−１−プロパノー
ルの製造方法としては、アルカリ水溶液中で、３−メル
カプト−１−プロパノールを硫酸ジメチルと反応させる
方法（J. Chem. Soc., (1927), 2498)、３−クロロ−１
−プロパノールとメタンチオールを水酸化ナトリウム水
溶液中で反応させる方法（J. Org. Chem., 26 (1961),
1463）、３−メルカプト−１−プロパノールとヨードメ
タンを炭酸ナトリウム存在下に、アセトン中で反応させ
る方法（Tetrahedron, 48 (1992) 28, 5933)等がある。As a method for producing 3-alkylthio-1-propanol, 3-mercapto-1-propanol is reacted with dimethyl sulfate in an aqueous alkaline solution (J. Chem. Soc., (1927), 2498). ), 3-chloro-1
-Method of reacting propanol and methanethiol in aqueous sodium hydroxide solution (J. Org. Chem., 26 (1961),
1463), a method of reacting 3-mercapto-1-propanol and iodomethane in acetone in the presence of sodium carbonate (Tetrahedron, 48 (1992) 28, 5933) and the like.
【０００４】しかしながら、これらの３−アルコキシ
（又は３−アルキルチオ）−１−プロパノールの製造方
法は、いずれも１，３−プロパンジオール又はその誘導
体という高価な原料を使用しているため、経済性が悪
く、工業的な製造方法としては問題がある。However, these methods for producing 3-alkoxy (or 3-alkylthio) -1-propanol all use expensive raw materials such as 1,3-propanediol or a derivative thereof, and thus are economical. Poor, there is a problem as an industrial manufacturing method.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、上記の問題
を解決し、安価であり、かつ工業的に入手が容易な化合
物を出発物質として、高純度の３−置換−１−プロパノ
ールを製造する方法を提供することを目的とする。DISCLOSURE OF THE INVENTION The present invention solves the above-mentioned problems and provides a high-purity 3-substituted-1-propanol starting from a low-cost, industrially easily available compound. The purpose is to provide a way to:
【０００６】[0006]
【課題を解決するための手段】本発明者らは、上記課題
の解決手段について鋭意検討を行った結果、安価であ
り、かつ入手が容易な３−アルコキシ（又は３−アルキ
ルチオ）−１−プロピルアミンを使用し、これをジアゾ
化して分解することにより、容易に高純度の３−アルコ
キシ（又は３−アルキルチオ）−１−プロパノールを製
造できることを見出し、本発明に到達した。Means for Solving the Problems As a result of intensive studies on the means for solving the above problems, the present inventors have found that inexpensive 3-alkoxy (or 3-alkylthio) -1-propyl is easily available. The inventors have found that a high-purity 3-alkoxy (or 3-alkylthio) -1-propanol can be easily produced by using an amine, diazotizing it and decomposing it, and arrived at the present invention.
【０００７】すなわち、本発明は、一般式： ＲＺ（ＣＨ2)3 ＮＨ2 （１） （式中、Ｒは、低級アルキル基であり、Ｚは、Ｏ又はＳ
である）で表されるアミンを亜硝酸類と反応させ、得ら
れたジアゾニウム塩を分解することを特徴とする、一般
式： ＲＺ（ＣＨ2)3 ＯＨ （２） （式中、Ｒ及びＺは前記と同じである）で表される３−
アルコキシ（又は３−アルキルチオ）−１−プロパノー
ルの製造方法に関する。That is, the present invention provides a compound represented by the general formula: RZ (CH 2 ) 3 NH 2 (1) (wherein R is a lower alkyl group, and Z is O or S
Wherein the amine represented by the formula is reacted with nitrites to decompose the resulting diazonium salt, wherein RZ (CH 2 ) 3 OH (2) (wherein R and Z Is the same as described above).
The present invention relates to a method for producing an alkoxy (or 3-alkylthio) -1-propanol.
【０００８】式（１）及び式（２）の化合物において、
Ｒで示される低級アルキル基は、炭素数１〜５の直鎖状
又は分岐状アルキル基である。In the compounds of the formulas (1) and (2),
The lower alkyl group represented by R is a linear or branched alkyl group having 1 to 5 carbon atoms.
【０００９】式（１）のアミンとしては、３−メトキシ
−１−プロピルアミン、３−エトキシ−１−プロピルア
ミン、３−ｎ−プロポキシ−１−プロピルアミン、３−
iso−プロポキシ−１−プロピルアミン、３−ｎ−ブト
キシ−１−プロピルアミン、３−tert−ブトキシ−１−
プロピルアミン、３−ｎ−ペンチルオキシ−１−プロピ
ルアミン、３−メチルチオ−１−プロピルアミン、３−
エチルチオ−１−プロピルアミン、３−ｎ−プロピルチ
オ−１−プロピルアミン、３−iso −プロピルチオ−１
−プロピルアミン、３−ｎ−ブチルチオ−１−プロピル
アミン、３−tert−ブチルチオ−１−プロピルアミン、
３−ｎ−ペンチルチオ−１−プロピルアミン等が挙げら
れる。The amine of the formula (1) includes 3-methoxy-1-propylamine, 3-ethoxy-1-propylamine, 3-n-propoxy-1-propylamine,
iso-propoxy-1-propylamine, 3-n-butoxy-1-propylamine, 3-tert-butoxy-1-
Propylamine, 3-n-pentyloxy-1-propylamine, 3-methylthio-1-propylamine, 3-
Ethylthio-1-propylamine, 3-n-propylthio-1-propylamine, 3-iso-propylthio-1
-Propylamine, 3-n-butylthio-1-propylamine, 3-tert-butylthio-1-propylamine,
3-n-pentylthio-1-propylamine and the like.
【００１０】また、式（２）の化合物としては、３−メ
トキシ−１−プロパノール、３−エトキシ−１−プロパ
ノール、３−ｎ−プロポキシ−１−プロパノール、３−
iso−プロポキシ−１−プロパノール、３−ｎ−ブトキ
シ−１−プロパノール、３−tert−ブトキシ−１−プロ
パノール、３−ｎ−ペントキシ−１−プロパノール、３
−メチルチオ−１−プロパノール、３−エチルチオ−１
−プロパノール、３−ｎ−プロピルチオ−１−プロパノ
ール、３−iso −プロピルチオ−１−プロパノール、３
−ｎ−ブチルチオ−１−プロパノール、３−tert−ブチ
ルチオ−１−プロパノール、３−ｎ−ペンチルチオ−１
−プロパノール等が挙げられる。The compounds of the formula (2) include 3-methoxy-1-propanol, 3-ethoxy-1-propanol, 3-n-propoxy-1-propanol, 3-methoxy-1-propanol,
iso-propoxy-1-propanol, 3-n-butoxy-1-propanol, 3-tert-butoxy-1-propanol, 3-n-pentoxy-1-propanol, 3
-Methylthio-1-propanol, 3-ethylthio-1
-Propanol, 3-n-propylthio-1-propanol, 3-iso-propylthio-1-propanol, 3
-N-butylthio-1-propanol, 3-tert-butylthio-1-propanol, 3-n-pentylthio-1
-Propanol and the like.
【００１１】本発明の方法では、直接合成法により、す
なわち、式（１）のアミンと亜硝酸類の反応により得ら
れるジアゾニウム塩を、水中で分解して、直接、式
（２）の３−置換−１−プロパノールを得ることが可能
である。In the method of the present invention, a diazonium salt obtained by a direct synthesis method, that is, a reaction of an amine of the formula (1) with a nitrite is decomposed in water to directly form a 3-azo compound of the formula (2). It is possible to obtain substituted-1-propanol.
【００１２】または、該ジアゾニウム塩の分解をカルボ
ン酸中で行うことにより、該ジアゾニウム塩の分解生成
物とカルボン酸とのカップリングを行わせ、相当するエ
ステルとした後、加水分解等の手段を用いて、目的とす
る３−置換−１−プロパノールを得る二段階合成法を用
いることもできる。この二段階合成法は、上記の直接合
成法で問題となる、水に易溶である３−置換−１−プロ
パノールと水との困難な分離を回避でき、３−置換−１
−プロパノールの合成方法として有用である。Alternatively, the decomposition of the diazonium salt is carried out in a carboxylic acid, whereby the decomposition product of the diazonium salt is coupled with the carboxylic acid to form a corresponding ester, and then a means such as hydrolysis is used. Can be used to obtain a desired 3-substituted-1-propanol. This two-step synthesis method can avoid difficult separation between water and the 3-substituted-1-propanol which is easily soluble in water, which is a problem in the above direct synthesis method, and can avoid the 3-substituted-1 method.
-Useful as a method for synthesizing propanol.
【００１３】本発明によりジアゾニウム塩を生成させる
には、式（１）のアミンを酸の付加塩とした後、酸性溶
媒中で亜硝酸類を反応させて得られる。In order to produce a diazonium salt according to the present invention, the diazonium salt is obtained by converting an amine of the formula (1) into an acid addition salt and then reacting with nitrous acid in an acidic solvent.
【００１４】ジアゾニウム塩の生成分解反応は、−１０
〜８０℃、好ましくは０〜４５℃で行い、さらに、温度
を５０〜８０℃に上昇させて反応を完結させる。The formation and decomposition reaction of the diazonium salt is -10
The reaction is carried out at -80 ° C, preferably 0-45 ° C, and the temperature is raised to 50-80 ° C to complete the reaction.
【００１５】二段階合成法におけるジアゾニウム塩の分
解生成物とカルボン酸とのカップリング工程は、ジアゾ
ニウム塩生成反応の反応条件と同様の条件下で行われ
る。The step of coupling the decomposition product of the diazonium salt with the carboxylic acid in the two-step synthesis method is carried out under the same conditions as the reaction conditions for the diazonium salt formation reaction.
【００１６】原料アミンをジアゾ化する際に使用する亜
硝酸類として好適なものは、亜硝酸ナトリウム、亜硝酸
カリウム等のアルカリ金属塩、亜硝酸カルシウム、亜硝
酸バリウム等のアルカリ土類金属塩、及び三酸化窒素又
は酸化窒素と二酸化窒素との等モル混合物等が挙げられ
る。Preferred as nitrites used for diazotizing the starting amine are alkali metal salts such as sodium nitrite and potassium nitrite, alkaline earth metal salts such as calcium nitrite and barium nitrite, and Nitric oxide or an equimolar mixture of nitric oxide and nitrogen dioxide can be used.
【００１７】本発明において、亜硝酸類の使用量は、式
（１）のアミン１モル当り通常１〜５モル、好ましくは
１．２５〜３モルの範囲である。In the present invention, the amount of the nitrite used is usually 1 to 5 mol, preferably 1.25 to 3 mol, per 1 mol of the amine of the formula (1).
【００１８】アミンの塩を生成させる酸は、塩酸、硫
酸、リン酸等の無機強酸及び、ギ酸、酢酸、プロピオン
酸、シュウ酸、コハク酸、クエン酸、メタンスルホン
酸、ベンゼンスルホン酸等の有機酸が好ましい。これら
の酸の使用量は、原料アミン１モル当り１モル〜５モ
ル、好ましくは１〜３モルの範囲である。Acids that form amine salts include inorganic strong acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, succinic acid, citric acid, methanesulfonic acid and benzenesulfonic acid. Acids are preferred. The amount of the acid used is in the range of 1 mol to 5 mol, preferably 1 mol to 1 mol, per 1 mol of the raw material amine.
【００１９】本発明のジアゾニウム塩の生成反応時に用
いる適切な溶媒として、原料アミンから一工程で目的物
を得る直接合成法の場合は、水又は低級アルコール類
（例えば、メタノール、エタノール、エチレングリコー
ル、メチルセロソルブ等）やジオキサン、モノグライム
のような非プロトン性の溶媒等と水との混合物が挙げら
れる。水が好ましい。In the case of the direct synthesis method in which the desired product is obtained in one step from the starting amine, water or lower alcohols (for example, methanol, ethanol, ethylene glycol, A mixture of water and an aprotic solvent such as methylcellosolve), dioxane and monoglyme. Water is preferred.
【００２０】本発明の二段階合成法でのジアゾニウム塩
の生成反応時に用いる適切な溶媒として、常温付近で液
状の有機カルボン酸類、特に酢酸、プロピオン酸が好適
であり、これらの酸と他の溶媒、例えばジオキサン、モ
ノグライム、ＴＨＦ等、との混合物が挙げられる。As a suitable solvent used in the reaction for forming a diazonium salt in the two-step synthesis method of the present invention, organic carboxylic acids which are liquid at about room temperature, especially acetic acid and propionic acid, are suitable. For example, a mixture with dioxane, monoglyme, THF and the like can be mentioned.
【００２１】[0021]
【実施例】以下に実施例を挙げて本発明をさらに詳細に
説明するが、本発明はこれらの実施例に限定されるもの
ではない。EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００２２】実施例１ 氷酢酸４００mlに３−メトキシ−１−プロピルアミン１
００ｇを、１０℃以下の温度で、撹拌しながら加え、次
いで亜硝酸ナトリウム１００ｇ及び酢酸亜鉛二水和物１
２．３ｇを、４０℃以下の温度に保ちながら加え、一夜
撹拌を続けた。反応液を、６０℃まで加熱して、１０分
間撹拌後、氷冷し、析出した結晶をろ別した。ろ残を酢
酸エチルで洗浄し、洗浄液とろ液を合わせ、減圧蒸溜に
より、ｂｐ14５５〜６０℃の３−メトキシ−１−プロピ
ルアセテート１０４ｇを得た。 ＧＣ純度：９２．５％、 1Ｈ ＮＭＲ（ＣＤＣｌ3)：δ
〔ppm 〕＝1.88 (2H, m), 2.03 (3H, s), 3.30 (3H,
s), 3.45 (2H, m), 4.12 (2H, t)Example 1 3-methoxy-1-propylamine 1 in 400 ml of glacial acetic acid
00g with stirring at a temperature below 10 ° C., then 100 g of sodium nitrite and 1 g of zinc acetate dihydrate.
2.3 g was added keeping the temperature below 40 ° C. and stirring was continued overnight. The reaction solution was heated to 60 ° C., stirred for 10 minutes, cooled on ice, and the precipitated crystals were separated by filtration. The residue was washed with ethyl acetate, and the combined washings and filtrate were distilled under reduced pressure to obtain 104 g of 3-methoxy-1-propyl acetate at bp 14 of 55 to 60 ° C. GC purity: 92.5%, 1 H NMR (CDCl 3 ): δ
[Ppm] = 1.88 (2H, m), 2.03 (3H, s), 3.30 (3H,
s), 3.45 (2H, m), 4.12 (2H, t)
【００２３】このうち、３−メトキシ−１−プロピルア
セテート５０ｇを反応器に仕込み、メタノール２００ml
及びｐ−トルエンスルホン酸一水和物１ｇを加えて、
５．５時間還流した。メタノールを常圧で留去した後、
残留物の減圧蒸溜により、ｂｐ 18５９〜６１℃の３−メ
トキシ−１−プロパノール４１．２ｇを得た。 ＧＣ純度：９８．５％、 1Ｈ ＮＭＲ（ＣＤＣｌ3)：δ
〔ppm 〕＝1.83 (2H, m), 3.39 (3H, s), 3.35-3.87 (5
H, m)Among them, 3-methoxy-1-propyl alcohol
50 g of acetate is charged to the reactor, and 200 ml of methanol is charged.
And 1 g of p-toluenesulfonic acid monohydrate,
Refluxed for 5.5 hours. After distilling off methanol at normal pressure,
Bp by distillation of the residue under reduced pressure 183-Me at 59-61 ° C
41.2 g of toxic-1-propanol were obtained. GC purity: 98.5%,1H NMR (CDClThree): Δ
[Ppm] = 1.83 (2H, m), 3.39 (3H, s), 3.35-3.87 (5
H, m)
【００２４】実施例２ ３−メトキシ−１−プロピルアミン１７．８ｇ、硫酸１
１．８ｇ及び水２０mlを反応器に仕込み、水３０mlに溶
解した亜硝酸ナトリウム１６．６ｇの水溶液を３５℃以
下の温度で加え、一夜撹拌を続けた。希硫酸でpH３にし
た反応液を蒸留し、ｂｐ35３４〜３６℃の留液に炭酸カ
リウムを飽和させて、エタノールで抽出した。エタノー
ルを常圧で留去し、３−メトキシ−１−プロパノール
３．２ｇを得た。 ＧＣ純度：９８．２％Example 2 17.8 g of 3-methoxy-1-propylamine, sulfuric acid 1
1.8 g and 20 ml of water were charged into a reactor, and an aqueous solution of 16.6 g of sodium nitrite dissolved in 30 ml of water was added at a temperature of 35 ° C. or lower, and stirring was continued overnight. The reaction solution, which was adjusted to pH 3 with dilute sulfuric acid, was distilled, and the distillate at bp 35 of 34 to 36 ° C. was saturated with potassium carbonate and extracted with ethanol. Ethanol was distilled off under normal pressure to obtain 3.2 g of 3-methoxy-1-propanol. GC purity: 98.2%
【００２５】実施例３ 氷冷した３−メチルチオ−１−プロピルアミン２４．５
ｇに、酢酸１００mlを少量ずつ加え、次いで亜硝酸ナト
リウム２１．１ｇ及び酢酸亜鉛二水和物２．６ｇを４５
℃以下の温度で加えた後、７０℃に加熱し、３０分間撹
拌した。室温で一夜撹拌後、氷冷して、析出した結晶を
ろ別し、ろ残を少量の酢酸エチルで洗浄した後、ろ液と
洗浄液を合わせ、減圧濃縮した。残渣を酢酸エチルで抽
出し、溶媒を留去し、得られた残留物を減圧蒸留して、
ｂｐ12８３〜８８℃の３−メチルチオ−１−プロピルア
セテート２２．１ｇを得た。1 Ｈ ＮＭＲ（ＣＤＣｌ3)：δ〔ppm 〕＝1.94 (2H, m),
2.06 (3H, s), 2.12 (3H, s), 2.60 (2H, m), 4.20 (2
H, t)Example 3 Ice-cooled 3-methylthio-1-propylamine 24.5
100 g of acetic acid was added in small portions to the resulting mixture, and 21.1 g of sodium nitrite and 2.6 g of zinc acetate dihydrate were added to 45 g of the mixture.
After adding at a temperature of not more than 0 ° C, the mixture was heated to 70 ° C and stirred for 30 minutes. After stirring overnight at room temperature, the mixture was cooled on ice, and the precipitated crystals were collected by filtration. The residue was washed with a small amount of ethyl acetate, and the filtrate and the washings were combined and concentrated under reduced pressure. The residue was extracted with ethyl acetate, the solvent was distilled off, and the obtained residue was distilled under reduced pressure.
to give 3-methylthio-1-propyl acetate 22.1g of bp 12 83 to 88 ° C.. 1 H NMR (CDCl 3 ): δ [ppm] = 1.94 (2H, m),
2.06 (3H, s), 2.12 (3H, s), 2.60 (2H, m), 4.20 (2
H, t)
【００２６】得られた３−メチルチオ−１−プロピルア
セテート２２．１ｇを、２８％アンモニア水３０mlと共
に反応器に仕込み、室温で二昼夜撹拌した。反応液を減
圧蒸留してｂｐ10８３〜８７℃の３−メチルチオ−１−
プロパノール１０．８ｇを得た。1 Ｈ ＮＭＲ（ＣＤＣｌ3)：δ〔ppm 〕＝1.90 (2H, m),
2.12 (3H, s), 2.63 (2H, m), 3.09 (1H, s), 3.75 (2
H, t)22.1 g of the obtained 3-methylthio-1-propyl acetate was charged into a reactor together with 30 ml of 28% aqueous ammonia and stirred at room temperature for two days. The reaction mixture was distilled under reduced pressure bp 10 83 to 87 of ° C. 3- methylthio-1-
10.8 g of propanol were obtained. 1 H NMR (CDCl 3 ): δ [ppm] = 1.90 (2H, m),
2.12 (3H, s), 2.63 (2H, m), 3.09 (1H, s), 3.75 (2
H, t)
【００２７】[0027]
【発明の効果】本発明の方法によれば、医農薬の中間体
として有用な式（２）の３−アルコキシ（又は３−アル
キルチオ）−１−プロパノールを、安価で、かつ工業的
に入手が容易な原料を用いて、従来法に比べ安易に、よ
り高純度で製造することができる。According to the method of the present invention, 3-alkoxy (or 3-alkylthio) -1-propanol of the formula (2), which is useful as an intermediate for medicinal and agricultural chemicals, can be obtained at low cost and industrially. It can be produced easily and with higher purity by using easy raw materials as compared with the conventional method.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭64−79133（ＪＰ，Ａ) 特開 平８−113546（ＪＰ，Ａ) Ｔｅｔｒａｈｅｄｒｏｎ，1992，Ｖｏ ｌ．48，Ｎｏ．28，Ｐ5933−5940 (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 41/26 C07C 43/13 C07C 319/20 C07C 323/12 C07C 29/09 C07C 67/00 C07C 245/12 C07C 245/20 C07B 41/02 ────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-64-79133 (JP, A) JP-A-8-113546 (JP, A) Tetrahedron, 1992, Vol. 48, No. 28, P5933-5940 (58) Fields investigated (Int. Cl. 7 , DB name) C07C 41/26 C07C 43/13 C07C 319/20 C07C 323/12 C07C 29/09 C07C 67/00 C07C 245/12 C07C 245/20 C07B 41/02
Claims (1)
である）で表されるアミンを、酸性溶媒中で亜硝酸類と
反応させ、得られたジアゾニウム塩の分解をカルボン酸
中で行うことにより、該ジアゾニウム塩の分解生成物と
カルボン酸とでカップリングを行わせ、相当するエステ
ルとした後、加水分解して、一般式： ＲＺ（ＣＨ2)3 ＯＨ （２） （式中、Ｒ及びＺは前記と同じである）で表される３−
置換−１−プロパノールを得ることを特徴とする３−置
換−１−プロパノールの製造方法。1. A general formula: RZ (CH 2 ) 3 NH 2 (1) wherein R is a lower alkyl group and Z is O or S
Is reacted with nitrites in an acidic solvent, and the resulting diazonium salt is decomposed in a carboxylic acid, whereby the decomposition product of the diazonium salt and the carboxylic acid are cupped. A ring is formed to give a corresponding ester, which is then hydrolyzed to give a compound represented by the general formula: RZ (CH 2 ) 3 OH (2) wherein R and Z are the same as defined above.
A process for producing 3-substituted-1-propanol, which comprises obtaining substituted-1-propanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13058097A JP3357570B2 (en) | 1997-05-21 | 1997-05-21 | Method for producing 3-substituted-1-propanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13058097A JP3357570B2 (en) | 1997-05-21 | 1997-05-21 | Method for producing 3-substituted-1-propanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10316605A JPH10316605A (en) | 1998-12-02 |
| JP3357570B2 true JP3357570B2 (en) | 2002-12-16 |
Family
ID=15037625
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13058097A Expired - Lifetime JP3357570B2 (en) | 1997-05-21 | 1997-05-21 | Method for producing 3-substituted-1-propanol |
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| Country | Link |
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| JP (1) | JP3357570B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6531635B1 (en) | 1999-05-18 | 2003-03-11 | Idemitsu Petrochemicals Co., Ltd. | Precursors of 3-alkoxyalkanols and processes for the preparation of 3-alkoxyalkanols |
| JP2001294544A (en) * | 2000-04-11 | 2001-10-23 | Tosoh Corp | Method for producing omega-methoxy-1-alkanol |
-
1997
- 1997-05-21 JP JP13058097A patent/JP3357570B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Ｔｅｔｒａｈｅｄｒｏｎ，１９９２，Ｖｏｌ．４８，Ｎｏ．２８，Ｐ５９３３−５９４０ |
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| Publication number | Publication date |
|---|---|
| JPH10316605A (en) | 1998-12-02 |
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