JPS58146537A - Preparation of 4-hydroxyphenylacetamide - Google Patents
Preparation of 4-hydroxyphenylacetamideInfo
- Publication number
- JPS58146537A JPS58146537A JP2986882A JP2986882A JPS58146537A JP S58146537 A JPS58146537 A JP S58146537A JP 2986882 A JP2986882 A JP 2986882A JP 2986882 A JP2986882 A JP 2986882A JP S58146537 A JPS58146537 A JP S58146537A
- Authority
- JP
- Japan
- Prior art keywords
- acetamide
- reaction
- hydroxyphenylacetic acid
- water
- hydroxyphenylacetamide
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
４−ヒドロキシフェニルアセトアミドは医薬、農薬の中
間体として有用な化合物である。DETAILED DESCRIPTION OF THE INVENTION 4-Hydroxyphenylacetamide is a compound useful as an intermediate for pharmaceuticals and agricultural chemicals.
しかして、該アミドの製造法としては４−ヒドロキシフ
ェニル酢酸エステルをアンモニアでアミド化する方法、
４−ヒドロキシフェニルエタノンをアンモニクムスルフ
イドでアミド化する方法等が知られている。Therefore, the method for producing the amide includes a method of amidating 4-hydroxyphenylacetic acid ester with ammonia,
A method of amidating 4-hydroxyphenylethanone with ammonium sulfide is known.
しかしながら、かかる方法は目的物の収率面あるいけ反
応操作面で工業的実施に＃ｉ問題が多い〇
しかるに本発明者等Ｆｉ４−ヒドロキシフェニルアセト
アミドを収率良＜、シかも簡単な操作で製造し得る方法
を見出すべく鋭意研究を重ねた結果、４−ヒドロキシフ
ェニル酢酸とアセトアミドを反応させる場合、容易にそ
の目的が達成出来ることを見出し本発明を完成した。However, such a method has many problems in industrial implementation in terms of yield of the target product and reaction operation.However, the present inventors have been able to produce Fi4-hydroxyphenylacetamide in good yield and with simple operations. As a result of intensive research to find a possible method, the present invention was completed by discovering that the object can be easily achieved when 4-hydroxyphenylacetic acid and acetamide are reacted.
４−ヒドロキシフェニル酢酸とアセトアミドとの反Ｉ１
５は両原料を混合し、１５０℃以上、好ましくＦｉ１５
０℃〜２５０℃程度に加熱すれば良い。Reaction of 4-hydroxyphenylacetic acid and acetamide I1
5 is a mixture of both raw materials, heated to 150°C or higher, preferably Fi15.
It may be heated to about 0°C to 250°C.
反応１ｉ溶融状態で進行する。１５０℃以下では反応速
度が低下し、一方２５０℃以上では副生物の生成が多く
なる。必要であれば反応時にアミルアルコール、シクロ
ヘキナノール、キシレン、テトラリン等の溶剤を共存さ
せることが出来る。反応時間＃ｉ２時間程度で充分であ
る。４−ヒドロキシフェニル酢酸とアセトアミドの使用
割合Ｆｉ４−ヒドロキシフェニル酢酸１モルに対しアセ
トアミドを１〜２０モル好ましくａ５〜１０モル用いる
のが適当である。Reaction 1i proceeds in the molten state. At temperatures below 150°C, the reaction rate decreases, while at temperatures above 250°C, more by-products are produced. If necessary, a solvent such as amyl alcohol, cyclohequinanol, xylene, or tetralin may be present during the reaction. A reaction time #i of about 2 hours is sufficient. Ratio of 4-hydroxyphenylacetic acid and acetamide used: Fi It is appropriate to use 1 to 20 moles of acetamide per 1 mole of 4-hydroxyphenylacetic acid, preferably 5 to 10 moles.
反応終了後は生成液に加水するか、生成液を蒸留して未
反応のアセトアミドを留去したのちの蒸留残液に加水す
ると４−ヒドロキシフェニルアセトアミドの結晶が析出
する。加水量は生成液又は蒸留残液に対し５０〜５００
容量％程度が適当である。After completion of the reaction, water is added to the product solution, or when the product solution is distilled to remove unreacted acetamide and water is added to the distillation residue, crystals of 4-hydroxyphenylacetamide are precipitated. The amount of water added is 50 to 500 to the product liquid or distillation residue.
Approximately % by volume is appropriate.
析出した結晶をＦ別、水洗して目的物を得る。The precipitated crystals are separated from F and washed with water to obtain the desired product.
必要に応じて再結晶、活性炭処理等の任意の精製操作を
実施し得る。Arbitrary purification operations such as recrystallization and activated carbon treatment may be performed as necessary.
得られる４−ヒドロキシフェニルアセトアミドは医薬、
農薬等の中間体として用いられる。The resulting 4-hydroxyphenylacetamide can be used as a pharmaceutical,
Used as an intermediate for agricultural chemicals, etc.
次に実例を挙げて本発明の方法を更に詳しく説明する。Next, the method of the present invention will be explained in more detail by giving examples.
実施例１
４−ヒドロキシフェニル酢酸１５．２ Ｆ （０，１モ
ル）とアセトアミド５９．Ｏｙ （１，０モル）とを混
合し、９０℃に加熱して均一溶融液とし丸。徐々に昇温
を行ない２００〜２１６℃の温度でＳ時間撹拌下に反応
を行った。Example 1 15.2 F (0.1 mol) of 4-hydroxyphenylacetic acid and 59.2 F of acetamide. Oy (1.0 mol) and heated to 90°C to form a homogeneous melt. The temperature was gradually raised and the reaction was carried out at a temperature of 200 to 216° C. for S hours with stirring.
反応生成液を真空蒸留し未反応のアセトアミドを留去し
た。缶残液に２０−の水を加えて８０′Ｃに昇温し１０
分間撹拌した。該液を５℃で一晩放置し、析出した結晶
をＦ別し水洗、乾燥して淡褐色の固体１５．５ ｆを得
た。The reaction product liquid was vacuum distilled to remove unreacted acetamide. Add 20 - of water to the remaining liquid in the can and raise the temperature to 80'C.
Stir for a minute. The liquid was left at 5°C overnight, and the precipitated crystals were separated by F, washed with water, and dried to obtain 15.5 f of a light brown solid.
高速液体クロマトグラフィーによる分析でこのもの＃：
ｔ９２％の４−ヒドロキシフェニルアセトアミドを含ん
でいることが確認された。This one analyzed by high performance liquid chromatography:
It was confirmed that it contained 4-hydroxyphenylacetamide with a content of 92%.
収率は仕込みの４−ヒドロキシフェニル酢酸ニ対し８２
９６であった。The yield is 82% based on the starting 4-hydroxyphenylacetic acid.
It was 96.
水で再結晶した白色リン片状結晶の融点け１７４〜１７
５℃であった。Melting point of white scaly crystals recrystallized from water: 174-17
The temperature was 5°C.
実施例２
４−ヒドロキシフェニル酢酸７．６１！ （０，０５モ
ル）とアセトアミド１１．８ ｆ （０，２モル）を混
合し９０℃に加熱して均一溶融液とした。徐々に昇温し
２００℃〜２１６℃の温度で４時間撹拌下に反応を行う
九。Example 2 4-Hydroxyphenylacetic acid 7.61! (0.05 mol) and 11.8 f (0.2 mol) of acetamide were mixed and heated to 90°C to form a homogeneous melt. 9. The reaction is carried out with stirring for 4 hours at a temperature of 200°C to 216°C with gradual heating.
反応終了後、生成液が１００℃になった時点で１５ｄの
水を加え１０分間撹拌すると結晶が析出した。５℃で一
液放置後、析出物をＦ別、水洗、乾燥し４−ヒドロキシ
フェニルアセトアミドを得た（収率６１％）。更ＫＷ液
及び洗液から４−ヒドロキシフェニルアセトアミドを回
収した。４−ヒドロキシフェニルアセトアミドの総合収
率ハ８９％であった。After the reaction was completed, when the temperature of the resulting solution reached 100° C., 15 d of water was added and stirred for 10 minutes to precipitate crystals. After allowing the solution to stand at 5°C, the precipitate was separated by F, washed with water, and dried to obtain 4-hydroxyphenylacetamide (yield: 61%). 4-Hydroxyphenylacetamide was recovered from the KW solution and washing solution. The overall yield of 4-hydroxyphenylacetamide was 89%.
Claims (1)
ることを特徴とする４−ヒドロキシフェニルアセトアミ
ドの製造方法。A method for producing 4-hydroxyphenylacetamide, which comprises reacting 4-hydroxyphenylacetate with acetamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2986882A JPS58146537A (en) | 1982-02-25 | 1982-02-25 | Preparation of 4-hydroxyphenylacetamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2986882A JPS58146537A (en) | 1982-02-25 | 1982-02-25 | Preparation of 4-hydroxyphenylacetamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58146537A true JPS58146537A (en) | 1983-09-01 |
| JPH0321020B2 JPH0321020B2 (en) | 1991-03-20 |
Family
ID=12287944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2986882A Granted JPS58146537A (en) | 1982-02-25 | 1982-02-25 | Preparation of 4-hydroxyphenylacetamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58146537A (en) |
-
1982
- 1982-02-25 JP JP2986882A patent/JPS58146537A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0321020B2 (en) | 1991-03-20 |
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