hydrophenantiirene (X). A.-A solution of ketone VI (57 g.) in ether (100 ml.) was added dropwise to a cold solution of methylmagnesium iodide prepared from magnesium (6.1 g.), methyl iodide (40 g.) and dry ether (300 ml.). After standing overnight the reaction mixture was treated with ammonium chloride solution and the ether layer was separated, washed with water and concentrated. The crude alcohol VII (60 g.) was dissolved in benzene (40 ml.) and cyclized with sulfuric acid (600 ml.) and water (126 ml.) as
PYROLYSIS OF ARYL GLYCOLIC ACIDS 973tracts was washed with 1% aqueous potassium hydroxide.The nitrobenzene soIution was treated with 75 g. of anhydrous sodium carbonate, and the resulting mixture was stirred for 18 hours. The dark red, filtered reaction mixture was subjected to distillation until the vapor temperature reached 205'; then it was steam distilled until the nitrobenzene was removed. The dark tars were separated from the aqueous residue in the distilling flask and extracted with benzene for three days in a Soxhlet apparatus. Fresh benzene then replaced the extract solution, and extraction was continued for three additional days. The combined extracts were allowed to flow through a 1 X 18 in. column of activated alumina, and the light yellow solution which emerged from the column was concentrated to 50 ml. On cooling, this solution deposited 5 g. (19%) of a solid mixture which gave evidence of containing a t least two compounds, one of which melted a t about 175" and the other a t about 270'.One 0.75-g. sample of the solid mixture was chromatographed on a 1 X 20 in. column of activated alumina from 1
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