Uses
Ethyl hydrogen pimelate is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.
Synthesis
3) Synthesis of 7-ethoxy-7-oxoheptanoic acid: potassium hydroxide (KOH, 16.8 g, 0.30 mol) was added to a solution of diethyl heptanedioate (65 g, 0.30 mol) in ethanol (400 mL). The reaction mixture was stirred at 80 °C for 24 h. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The concentrated mixture was poured into water and the pH of the aqueous solution was adjusted with concentrated sulfuric acid (H2SO4) to 1. The aqueous phase was extracted and the organic solvent was removed to give the crude product. The crude product was purified by fast column chromatography (silica gel SiO2 as stationary phase, eluent ratio of ethanol:ethyl acetate=1:10), and finally 7-ethoxy-7-oxoheptanoic acid was obtained (38 g, 67% yield).
References
[1] Patent: US2014/256775, 2014, A1. Location in patent: Paragraph 0178; 0183; 0184
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 2776 - 2785
[3] Bulletin de la Societe Chimique de France, 1910, vol. <4>7, p. 219
[4] Journal of the Chemical Society, 1901, vol. 79, p. 1192
[5] Bioorganic Chemistry, 1998, vol. 26, # 3, p. 157 - 168
