Analyzing the synthesis route of 101-32-6

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101-32-6, 2,2-(Benzylimino)diethanol, and friends who are interested can also refer to it.

Related Products of 101-32-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 101-32-6, name is 2,2-(Benzylimino)diethanol. A new synthetic method of this compound is introduced below.

Synthesis was performed according to the published procedure[17] with some alterations as mentioned below. 2,2′-(Benzylazanediyl)bis(ethan-1-ol) (759 mg, 3.89 mmol) in anhydrous THF (40 mL) was transferred into the two-necked flask under argon atmosphere. A solution of 1 M potassium tert-butoxide in THF(8.03 g, 71.56 mmol) was slowly injected into the reaction mixture. Pentaethylene glycol di(p-toluenesulfonate) (2.12 g, 3.89 mmol) was dissolved in anhydrous THF (20 mL) and added to the reaction mixture dropwise. The mixture was stirred for 2.5 h at 40 C. TLCanalysis (ethyl acetate/MeOH 5:1, Rf of 4 = 0.29) indicated that thereaction was completed immediately. THF was evaporated under reduced pressure. The product was dissolved in ethyl acetate (50 mL) and extracted with 5% hydrochloric acid (v/v) (3 x 50 mL).T he water layer was collected, and neutralized by 1 M NaOH and the product was extracted three times with ethyl acetate(3 x 80 mL). The organic layer was collected and evaporated todryness. The crude product was purified by column chromatographyon silica with ethyl acetate/MeOH/TEA 15:1:0.1 as an eluent. After some impurities were washed out, the mobile phase was changed to ethyl acetate/MeOH/TEA 15:3:1 as the eluent. Yield: 792 mg (51%) of colorless oil. 1H NMR (500 MHz, CDCl3, 25 C):d 2.74-2.93 (m, 4H, CH2), 3.59-3.72 (m, 26 H, CH2) and 7.22e7.41 ppm (m, 5 H, Bn-H); MS (APCI): m/z 398.7 [MH]. The other analytical data corresponded well with data published in the literature

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101-32-6, 2,2-(Benzylimino)diethanol, and friends who are interested can also refer to it.

Reference:
Article; Lochman, Lukas; Svec, Jan; Roh, Jaroslav; Novakova, Veronika; Dyes and Pigments; vol. 121; (2015); p. 178 – 187;,
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