Tetrahydrofuran → 3-Allyloxy-4-methoxystyrene

Participants

Reaction Steps

Sodium amide (39 g) was dispersed in dry tetrahydrofuran (800 Dmls). Methyltriphenylphosphonium bromide (102 g) was added and the mixture stirred at R.T. for 2 hours. 3-allyloxy-4-methoxy-benzaldehyde (50 g) was then added dropwise over ca. 15 mins. and the mixture stirred for a further 3 hours. The mixture was filtered and the solvent removed from the filtrate under reduced pressure. The residue was washed with diethyl ether (1.51) and the solvent removed to yield a brown coloured resin. The washing process was repeated and the residue obtained was distilled under reduced pressure to give 3-allyloxy-4-methoxystyrene (29.5 g), b.p.98-104° C. at 0.8 mbar.

Provenance & Evidence