These common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, its 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. Application In Synthesis of Cinnamyl chloride
EXAMPLE 1 Obtaining 2-(3-N,N-diisopropylamine-1-phenylpropyl)-4-carboxyphenol (IV’a) Diisopropylamine (2.77 1, 19.65 mol) and sodium iodide (16.95 g, 0.13 mol) were loaded onto a solution of cinnamyl chloride (1 kg, 6.55 mol) in ethanol (3 1/kg) at 20/25C. The mixture was heated at internal 80-85C, the reaction conditions being maintained for 3-4 hours until the end of such reaction. The mixture was cooled at 40-45C and distilled to an internal volume of 1.3 1. The mixture was then cooled at 20-25C, water (4 1) and toluene (3 1) was added and the pH was adjusted to 1.0-1.5. The phases were decanted and dichloromethane (4 1) was loaded onto the aqueous phase, adjusting the pH again to 11.5-12.0. The phases were decanted and the organic phase was washed with water (4 1). Once the phases were decanted, the organic phase was distilled at atmospheric pressure to an internal volume of 1.3 1 in order to then load heptane (0.5 1). Again, it was distilled to 1.3 1 and heptane (2 1) was loaded. The suspension which was obtained was filtered by a prelayer, which was washed with heptane (0.5 1). The filtered organic phase was distilled at atmospheric pressure to an internal volume of 1.3 1. The amine content of the reaction mixture was determined by the potentiometric titration thereof. Acetic acid (1.2 l/kg of amine), 4-hydroxybenzoic acid (0.63 kg/kg of amine, 1 equivalent), and, then, sulfuric acid (1.1 l/kg of amine, 4.5 equivalents) were loaded onto the mixture. It was heated at internal 80-85C, the reaction conditions being maintained for 5-6 hours until the end of the reaction. The reaction mixture was cooled to 35-40C and water (10 l/kg of amine) and ethyl acetate (10 l/kg of amine) were loaded. The phases were decanted and the organic phase was washed out with water (5 l/kg). The aqueous phases were pooled; toluene (5 l/kg of amine) was loaded, the phases were decanted and n-butanol (10 l/kg of amine) was loaded onto the aqueous phase, the pH was adjusted to 7 and it was decanted. The organic phase was distilled to an internal amine volume of 1.5-2.0 l/kg and then heptane (8 l/kg of amine) was loaded. The product which crystallized was cooled at 5-10C, filtered and washed with heptane (5 l/kg of amine). The product was then dried in an oven with air circulation for 10-12 hours, obtaining a product with an overall molar yield of 40% and with a purity greater than 90%. NMR (1H) DMSO: H8: doublet 0.8-0.9 ppm 12H, H5: multiplet 2.0-2.1 ppm 2H, H6: multiplet 2.3 ppm 2H, H7: multiplet 2.8-3.0 ppm 2H, H4: triplet 4.3 ppm 1H, H1: doublet 6.8 ppm 1H, H11: multiplet 7.1 ppm 1H, H10-9: multiplet 7.1-7.3 ppm 4H, H2: doublet 7.5 ppm 1H, H3: singlet 7.8 ppm 1H. NMR(13C) DMSO: 20.52; 20.57; 30.74; 36.11; 39.72; 48.04; 114.35; 125.56; 126.43; 128.59; 128.68; 129.02; 129.47; 129.77, 145.34; 157.76; 169.90.
The synthetic route of Cinnamyl chloride has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Ragactives, S.L.U.; EP2281801; (2011); A1;,
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