4-(ethoxymethyl)-2,6-dimethylphenol | 58661-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(ethoxymethyl)-2,6-dimethylphenol
• 英文别名: 4-Hydroxy-3,5-dimethylbenzyl-ethyl-ether
• CAS: 58661-27-1
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: KAQRKQRTMLHHLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,4,6-三甲酚 以20%的产率得到
  参考文献：
  名称：

  ADLER E.; ANDERSSON G.; EDMAN E., ACTA CHEM. SCAND. , 1975, B29, NO 9, 909-920

  摘要：

  DOI：

文献信息

• The Oxidation of 2,4,6-Trimethylphenol with Molecular Oxygen Catalyzed by a Copper(II)-Oxime or Copper(II)-Amine System.
  作者：Masao Shimizu、Yoshihito Watanabe、Hideo Orita、Takashi Hayakawa、Katsuomi Takehira

  DOI：10.1246/bcsj.66.251

  日期：——

  2,4,6-Trimethylphenol (1a) was selectively oxidized to 3,5-dimethyl-4-hydroxybenzaldehyde (2a) by molecular oxygen in the presence of a copper(II) chloride-oxime or copper(II) chloride-amine catalyst in alcohol at ambient temperature. When an acid was present in the catalyst system, the formation of both 2,6-dimethyl-p-benzoquinone (3) and a formaldehyde dialkyl acetal was accelerated. It is likely that 2a is produced by way of the formation of a quinonemethide intermediate, followed by a repeated 1,6-addition of alcohol on the intermediate to form a 4-(alkoxymethyl)-2,6-dimethylphenol (5a), and then 3,5-dimethyl-4-hydroxybenzaldehyde dialkyl acetal, which would be hydrolyzed to 2a. When the reaction time was shortened, 5a was isolated in good yield. Oxidations of the other p-methyl-substituted phenols were also examined using the present oxidation system.

  2,4,6-三甲基苯酚（1a）在铜（II）氯化物-肟或铜（II）氯化物-胺催化剂的存在下，利用分子氧在酒精中于室温下可选择性地氧化为3,5-二甲基-4-羟基苯甲醛（2a）。当催化剂体系中存在酸时，2,6-二甲基对苯醌（3）和甲醛二烷基缩醛的形成会加速。2a很可能是通过形成醌亚甲基中间体，随后在中间体上重复进行1,6-加成反应，生成4-（烷氧基甲基）-2,6-二甲基苯酚（5a），然后形成3,5-二甲基-4-羟基苯甲醛二烷基缩醛，最终水解为2a。当反应时间缩短时，5a可以高收率地分离出来。通过本氧化体系对其他对位甲基取代苯酚的氧化反应进行了研究。
• A facile synthesis of 4-alkoxymethylphenols by a copper(II)-acetoxime catalyst/O2 system
  作者：Masao Shimizu、Yoshihito Watanabe、Hideo Orita、Takashi Hayakawa、Katsuomi Takehira

  DOI：10.1016/s0040-4039(00)78906-4

  日期：1991.4

  4-Alkoxymethyl-2,6-dimethylphenols were synthesized from 2,4,6-trimethylphenol in good yields by a copper(II) chloride-acetoxime catalyst/molecular oxygen system in alcohols at ambient temperature. The oxidation of the other p-methylsubstituted phenols were also examined.
• Adler,E. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1975, vol. 29, p. 909 - 920
  作者：Adler,E. et al.

  DOI：——

  日期：——