Electric Literature of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture of cinnamyl chloride (905 ml, 6.5 mol), diisopropylamine (1.37 1, 9.75 mol), potassium carbonate (0.90 kg, 6.5 mol), potassium iodide (54 g, 0.325 mol), toluene (2.1 l) and methanol (0.50 1) is stirred at reflux temperature for 20 hours. The mixture is cooled to 25 C and water (5.2 1) is added. Phases are separated and the organic phase is extracted with brine. Organic phase is concentrated under reduced pressure (50 C) and then water (10.4 1) and toluene (2.6 l) are added and the pH is adjusted to 2 by addition of concentrated hydrochloric acid (-500 ml). The resulting mixture is stirred for 15 minutes and the phases are separated. The aqueous phase is re-extracted twice with toluene (2 x 2.6 l). Then the pH of the aqueous phase is adjusted to 12 by addition of 8 M aqueous sodium hydroxide solution (750 ml). To the resulting white suspension is added heptane (5.2 l) and the mixture is stirred for 15 minutes. Phases are separated and aqueous phase is re-extracted twice with heptane (2 x 2.6 l). Combined organic phases are dried over Na2SO4 and concentrated to give 1.32 kg (93 % yield) of DIPCA.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Cinnamyl chloride, its application will become more common.
Reference:
Patent; LEK Pharmaceuticals d.d.; EP2364966; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics