Methanol → 1,5-Dichloro-9,10-dihydroanthracene

Participants

Reaction Steps

A mixture of 1,5-dichloro anthraquinone (49, 10 g, 36 mmol), red phosphorous (4.5 g, 145 mmol) and hydroiodic acid (47+%, 70 ml) in 470 ml of glacial acetic acid was refluxed under N2 for 4 days. The resulting mixture was cooled to room temperature and poured into 1 L of water to precipitate a violet colored solid. The solid was collected by filtration, dissolved in 800 ml of CH2Cl2, and filtered again. The filtrate was washed once with 100 ml of H2O, dried over Na2SO4 and concentrated under vacuum to yield the yellow colored, crude solid product. Methanol (100 ml) was added to this solid product and filtered again to collect white needles of the desired product (7.2 g, 80%). 1H NMR (300 MHz, CDCl3): δ 4.10 (s, 4H), 7.12-7.25 (m, 6H). 13C NMR (300 MHz, CDCl3): δ 32.93, 126.50, 127.13, 127.20, 133.15, 137.16.

Provenance & Evidence