The general procedure for the synthesis of 9,10-anthracenediol from anthraquinone was as follows: a mixture of anthraquinone (104 mg, 0.5 mmol) and sodium sulfide nonahydrate (480 mg, 2.0 mmol) in ethanol (30 mL) was reacted for 2 h at 78 °C with stirring under argon protection. Upon completion of the reaction, the mixture was cooled to 10 °C and the unreacted anthraquinone was removed by rapid filtration to afford the product 9,10-anthracenediol with a mass of 93 mg (90% yield). The anthraquinone present in the filtrate was oxidized and precipitated in air to give a final 10 mg (10% yield).
[1] Russian Journal of General Chemistry, 2008, vol. 78, # 8, p. 1529 - 1532
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 11, p. 780 - 781
[3] Tetrahedron, 2017, vol. 73, # 44, p. 6334 - 6340
[4] Russian Journal of Physical Chemistry, 1989, vol. 63, # 1, p. 91 - 94
[5] Zhurnal Fizicheskoi Khimii, 1989, vol. 63, p. 177 - 182