METHOD OF CONVERTING PRIMARY AMIDO-ALCOHOL INTO AMIDE CARBOXYLIC ACID IN HIGH YIELD BY USING WATER AS SOLVENT

• Main Authors: JOSE GUILLERMO ROSA, BIJAN HARICHIAN, CHEN HANG
• Format: Patent
• Language: English; Japanese
• Published: 15.10.2015
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

PROBLEM TO BE SOLVED: To provide an improved method of oxidizing a primary amido-alcohol into a corresponding amido-carboxylic acid in a high yield.SOLUTION: A method comprises reacting an amido-alcohol of formula (1) with an oxidant in the presence of a hindered nitroxide radical and, if necessary, a cocatalyst. The solvent consists of water alone, and the oxidant is distributed in water. The amido-alcohol stays in a solid organic phase or is distributed, leading to a high yield, and the alcohol containing an amido group is converted into a corresponding carboxylic acid in a yield of 75% or higher. Formula (1): R1-CONR2(CH2)mOH, where R1 is a 7-22C linear/branched alkyl or alkenyl group; R2 is H or a 1-6C alkyl or hydroxyalkyl group; m is an integer of 1-6. 【課題】第一級アミドアルコールを、対応するアミドカルボン酸へ高収率で酸化する改良された方法の提供。【解決手段】式（１）で表されるアミドアルコールを、ヒンダードニトロキシドラジカル及び場合により共触媒の存在下で酸化剤と反応させる方法。溶媒は水だけであり、酸化剤の存在下で、酸化剤を水の中に分配し、アミドアルコールは固体有機相中に留まるか又は分配され、これにより高収率を可能にし、アミド基を含むアルコールを、対応するカルボン酸に７５％以上の収率で変換する方法。Ｒ１−ＣＯＮＲ２（ＣＨ２）ｍＯＨ・・・（１）［Ｒ１はＣ７〜２２の直鎖／分枝のアルキル又はアルケニル基；Ｒ２はＨ又はＣ１−６個のアルキル或いはヒドロキシアルキル基；ｍは１から６の整数］【選択図】なし