2-methoxy-4-methylphenyl pentadecanoate

Pentadecanoic Acid (1.33 g, 5.5 mmol) was added to creosole (0.69 g, 5.0 mmol) with acetonitrile (15 mL), DMAP (0.0611 g, 0.5 mmol) and EDC.HCl (1.246, 6.5 mmol) resulting in a colourless solution that was refluxed for 2 hours using TLC to monitor the extent of reaction. An acid/base aqueous/organic work-up followed by washing the refluxed mixture added to hexane (20 mL) with HCl twice (2 x 20 mL, 1M), 10 wt% Sodium Bicarbonate twice (2 x 20 mL), water (20 mL) and saturated aqueous NaCl twice (2 x 20 mL) resulting in the separation of the organic phase, which was subsequently dried using MgSO4, filtered under gravity and evaporated in vacuo to afford a colourless oil. After this oil was allowed to stand, 2-methoxy-4-methylphenyl pentadecanoate acid crystallised in an exothermic reaction releasing heat to form small, white, solid crystals yielding the isolated product: 1.0 g (55.56%, 5 mmol)

将十五烷酸（Pentadecanoic Acid，1.33 g，5.5 mmol）与乙腈（acetonitrile，15 mL）、4-二甲氨基吡啶（4-Dimethylaminopyridine, DMAP，0.0611 g，0.5 mmol）以及1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐（1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDC·HCl，1.246 g，6.5 mmol）加入至愈创木酚（creosole，0.69 g，5.0 mmol）中，得到无色澄清溶液，随后回流反应2小时，通过薄层色谱（Thin Layer Chromatography, TLC）监测反应进程。随后对回流后的反应混合物进行酸碱水-有机相后处理：将反应液加入正己烷（20 mL）中，依次用1 mol/L盐酸（HCl，2×20 mL）洗涤两次、10 wt%碳酸氢钠（Sodium Bicarbonate）溶液（2×20 mL）洗涤两次、去离子水（20 mL）洗涤一次，再用饱和氯化钠（Sodium Chloride, NaCl）水溶液（2×20 mL）洗涤两次；分离得到有机相，经无水硫酸镁（Magnesium Sulfate, MgSO₄）干燥、常压重力过滤后减压旋蒸除去溶剂，得到无色油状粗产物。将该油状产物静置，其在放热反应中自发结晶并释放热量，最终形成细小的白色固体晶体，分离得到目标产物2-甲氧基-4-甲基苯基十五烷酸酯（2-methoxy-4-methylphenyl pentadecanoate）：1.0 g，收率55.56%（以5 mmol起始原料计）