3-(2,2-Dimethoxy-ethoxy)-4'-methoxy-4-methyl-biphenyl → 4-(4-Methoxyphenyl)-7-methylbenzofuran

Participants

Reaction Steps

A mixture of polyphosphoric acid (approx. 0.5 g) and chlorobenzene was brought to reflux and 3-(2,2-dimethoxy-ethoxy)-4′-methoxy-4-methyl-biphenyl (1.61 g, 5.33 mmol) in chlorobenzene (12 ml) was added dropwise. After 4 h the reaction was cooled, passed through a silica plug (the plug was washed with ether), and concentrated to 1.26 g (100%) of product as a light tan solid: mp 40–41° C.; 1H NMR (300 MHz, DMSO-d6): δ 2.50 (3H, s), 3.82 (3H, s), 7.03 (1H, d, J=2.2 Hz), 7.07 (2H, d, J=9.5 Hz), 7.19 (1H, d, J=8.1 Hz), 7.23 (1H, d, J=8.1 Hz), 7.56 (2H, d, J=9.5 Hz), 8.06 (1H, d, J=2.2 Hz).

Provenance & Evidence