Uses
1,3-Dimethoxy-2-propanol is a possbile antiknock additive for gasoline and diesel fuel. It is also used to prepare heteroarylcarbamoylbenzene derivatives as glucokinase activators.
Synthesis
According to an improved method described in the literature [15], 1,3-dimethoxy-2-propanol was synthesized by sodium hydroxide catalysis using methanol and 1-chloro-2,3-epoxypropane as raw materials. The procedure was as follows: 165 mL of anhydrous methanol and 11.4 g of sodium hydroxide were added to a 250 mL three-neck flask. The mixture was stirred and heated to reflux to form a homogeneous solution. 1-Chloro-2,3-epoxypropane (25.0 g) was added slowly and dropwise over a period of 1 hour. The reaction solution was kept at reflux for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with concentrated hydrochloric acid to 7. The precipitated sodium chloride was removed by filtration and the filtrate was fractionated under reduced pressure to afford 1,3-dimethoxy-2-propanol (29.8 g, 91.9% yield). The product was identified by 1H NMR (300 MHz, CDCl3): δ 3.92-3.99 (m, 1H, CH), 3.40-3.49 (m, 4H, CH2), 3.39 (s, 6H, CH3), and 2.59 (s, 1H, OH, the position and intensity of this peak varied with the concentration of the sample).13C NMR (75 MHz, CDCl3): δ 73.9 (CH2), 69.1 (CH), 59.0 (CH3). ESI-HRMS: m/z [M + Na]+ Calculated value: 143.0684 (C5H12O3 + Na), measured value: 143.0684. Elemental analysis results (C5H12O3): Calculated value: C 49.98%, H 10.07%; measured value: C 49.97%, H 9.84%.
References
[1] Chinese Chemical Letters, 2013, vol. 24, # 12, p. 1106 - 1108
[2] Organic Letters, 2017, vol. 19, # 11, p. 2789 - 2792
[3] Patent: WO2011/60228, 2011, A1. Location in patent: Page/Page column 69-70
[4] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1897, vol. <5> 6 II, p. 350
[5] Green Chemistry, 2015, vol. 17, # 8, p. 4326 - 4333
