Benzene, 1-(chloromethyl)-3(or 4)-ethenyl- → HCID 178418369, compound

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Reaction Conditions

Reaction Steps

Vinylbenzyl chloride (0.10 mole; 15.3 g, 60 percent meta-/40 percent para; Dow Experimental Monomer XC1915.00 stabilized with 5-butyl catechol (50 ppm) and nitromethane (700-1000 ppm)) was dissolved in 2-methoxyethanol (250 ml). This solution was added to a solution of sodium 5-phenyltetrazole (0.11 mole; 18.5 g) in 2-methoxyethanol and the reactants heated at 100° C. / 15 hours. The mixture was quenched with H2O (700 ml), extracted with CH2Cl2 (2×200 ml), the extracts washed with H2O (500 ml) and concentrated to give a viscous liquid (weight 26.0 g; 98.8 percent , yield). Mass spectral assay (electron impact and chemical ionization) showed a molecular weight ion peak at 262 (theor. 262.34). 13C NMR confirmed the presence of two isomers (3.65/1 ratio) corresponding to 2-vinylbenzyl 5-phenyltetrazole and 1-vinylbenzyl 5-phenyl-tetrazole. Elemental analysis found: C, 71.06; H, 5.42; N, 20.51; Cl, 1.43. Calculation for C16H14N4 : C, 73.26; H, 5.38; N, 21.38.

Provenance & Evidence