Piperonyl alcohol → 1,3-Benzodioxole, 5-(chloromethyl)-

Participants

Reaction Conditions

Reaction Steps

15.04 ml of thionyl chloride are added dropwise, at 0° C., over the space of 25 min and under argon, to 10.82 g of 3,4-methylenedioxybenzyl alcohol (Fluka, Buchs, Switzerland) and 48 g of diisopropylaminomethylpolystyrene (polyhunig base: polystyrene crosslinked with 2% divinylbenzene, diisopropylaminomethylated; Fluka, Buchs, Switzerland) in 200 ml of abs. ether. After having been stirred at 0° C. for a further 1.5 h, the mixture is filtered with suction and the filtrate is concentrated on a RE and then under HV. The residue is purified by chromatography on silica gel (eluent: C), and the title compound thus obtained. TLC Rf (hexane:ethyl acetate, 4:1)=0.47; 1H-NMR (200 MHz, CDCl3): 6.95-6.7(m, 3H), 5.97(s, 2H), 4.53(s, 2H).

Provenance & Evidence