Uses
1,7-Dichloroheptan-4-one is a useful research chemical.
Synthesis Reference(s)
Journal of the American Chemical Society, 78, p. 112, 1956
DOI: 10.1021/ja01582a034Organic Syntheses, Coll. Vol. 4, p. 278, 1963
Synthesis
The general procedure for the synthesis of 1,7-dichloro-4-heptanone from dicyclopropyl ketone was as follows: a 10-fold excess of HCl gas was passed into the dicyclopropyl ketone (15.00 g, 136.16 mmol) for 30 minutes. The reaction mixture was stirred at room temperature for 3 hours and then passed through HCl gas again for 30 minutes. Upon completion of the reaction, a brown oily crude product (24.93 g, 100% yield) was obtained, which could be used in subsequent steps without further purification. The structure of the product was confirmed by the following characterization data: 1H NMR (300 MHz, CDCl3) δ (ppm) 2.02 (m, 4H), 2.61 (t, 4H, J=7.0 Hz), 3.55 (t, 4H, J=6.3 Hz); 13C NMR (75 MHz, [D4] MeOH) δ (ppm) 27.6,40.3, 45.2,210.7; HRMS (APCI; MeOH) m/z (%) 183 (100); Calculated value for m/z [M + H]+ C7H13Cl2O+: 183.0337, measured value 183.0337. molecular formula: C7H12Cl2O (molecular weight 183.08).
References
[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 10, p. 4605 - 4618
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3957 - 3969
[3] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 7, p. 1218 - 1220
