HCID 21071774, compound → HCID 21071791, compound

Participants

Reaction Steps

To a 1 L 3-neck flask was added PPA (2.0 g), anhydrous chlorobenzene (300 ml) and the mixture was brought to reflux. Then 1-(2,2-dimethyoxy-ethoxy)-4-iodo-2-methyl benzene (11.16 g, 34.66 mmol) in chlorobenzene (80 ml) was slowly added by addition funnel over a 2 h period. The reaction was then cooled and passed through a silica plug (washed with chlorobenzene) and concentrated to a mixture of product plus 4-iodo-2-methylphenol. Column chromatography (100% hexane) afforded 4.49 g (53%) product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 2.44 (3H, s), 6.91 (1H, d, J=2.2 Hz), 7.46 (1H, brs), 7.86 (1H, d, J=1.2 Hz), 8.00 (1H, d, J=2.2 Hz); MS (E) m/z 258 ([M]+).

Provenance & Evidence