Pocahontas (LVB) coal, when treated with alkali metal in tetrahydrofuran in the presence of a small amount of naphthalene, is converted to a "coal anion." The coal anion is formed by transfer of negative charges from the alkali metal to the aromatic clusters in coal with naphthalene acting as an electron transfer agent. The coal anion, containing 12 charges per 100 carbon atoms, is readily alkylated by alkyl halides. The alkylated coals contain eight alkyl groups per 100 carbon atoms and are soluble in benzene at room temperature. Five of the alkyl groups are attached to carbon atoms and the remaining three to oxygen atoms. The molecular weight of the alkylated coals is in the same range (3,000-4,000) as that of petroleum asphaltenes. The solubility in benzene of alkylated coal and of petroleum asphaltenes is believed to be due to the presence of alkyl groups which prevent stacking of the aromatic clusters.