Ethyl α‐(Hydroxymethyl)acrylate
Ethyl α‐(Hydroxymethyl)acrylate
复制标题
α-(羟甲基)丙烯酸乙酯
DOI：
10.1002/047084289x.re090
复制
发表时间：
2001
影响因子：
0.7
通讯作者：
M. Villiéras
中科院分区：
文献类型：
--
作者：
J. Villiéras;M. Villiéras
C6 H10 O3（分子量130.16）
InChI = 1S/C6H10O3/c1-3-9-6（8）5（2）4-7/h7H，2-4H2，1H3
InChIKey = SYGAXBISYRORDR-UHFFFAOYSA-N
（聚合和共聚用官能化丙烯酸单体的重要来源;制备α-（卤甲基）丙烯酸酯、甲基丙烯酸酯和α-亚甲基内酯的中间体;强大的多官能迈克尔受体）
物理数据：bp 65-70 ℃/1 mmHg; nD 20 = 1.4494。
溶解度：水溶胶、乙醚、丙酮、乙醇、THF、氯仿。
制备方法： 在叔胺存在下，丙烯酸乙酯与甲醛水溶液发生羟甲基化反应（三乙胺，1，4-二氮杂双环[2.2.2]辛烷），3在微波辐射下，4或通过膦酰基乙酸三乙酯与甲醛在碳酸钾水溶液（当量1）存在下的Wittig-Horner反应。6已经发现用第一种方法会发生许多副反应，并且已经阐明了涉及醚形成的机理。7也描述了炔丙醇羰基化以产生这种试剂。8
（一）
纯化：通过减压蒸馏。
试剂纯度分析：通过GLC分析（例如2 m硅胶毛细管OV-1柱）; 1H NMR（CCl 4）4.20（2 H）、5.80和6.15（2 H）; 13 C NMR（CDCl 3）60.9、124.8、140.2和166.5。
处理、储存和注意事项：催泪、起泡和有毒。2应在通风良好的通风橱中戴手套处理该试剂。 建议在0 °C下避光储存。
[10029-04-6] C6H10O3 (MW 130.16)
InChI = 1S/C6H10O3/c1-3-9-6(8)5(2)4-7/h7H,2-4H2,1H3
InChIKey = SYGAXBISYRORDR-UHFFFAOYSA-N
(important source of functionalized acrylic monomers for polymerization and copolymerization; intermediate in the preparation of α-(halomethyl)acrylates, methacrylates, and α-methylene lactones; powerful polyfunctional Michael acceptor)
Physical Data: bp 65–70 °C/1 mmHg; nD20 = 1.4494.
Solubility: sol H2O, ether, acetone, alcohol, THF, chloroform.
Preparative Methods: by hydroxymethylation of Ethyl Acrylate with aqueous Formaldehyde solution in the presence of tertiary amines (Triethylamine, 1,4-Diazabicyclo[2.2.2]octane),3 under microwave radiation,4 or by the Wittig–Horner reaction of Triethyl Phosphonoacetate with formaldehyde in the presence of aqueous Potassium Carbonate (eq 1).5, 6 Many side reactions have been found to occur with the first method and the mechanism involving the formation of ethers has been elucidated.7 Carbonylation of propargyl alcohol to produce this reagent has also been described.8
(1)
Purification: by distillation at reduced pressure.
Analysis of Reagent Purity: by GLC analysis (e.g. 2 m silica capillary OV-1 column); 1H NMR (CCl4) 4.20 (2H), 5.80 and 6.15 (2H); 13C NMR (CDCl3) 60.9, 124.8, 140.2, and 166.5.
Handling, Storage, and Precautions: is lachrymatory, vesicatory, and toxic.2 This reagent should be handled with gloves in a well ventilated hood. Storage at 0 °C in the dark is recommended.