Rec~clion oJ Vitlyl Acelate arrd Toluerze\iiilyl acetate (S.Gg, 0.1 mole) mas added over a period of 1 hour to a coolcd mixture of toluene (92 g, 1.0 molc) ant1 aluininum chloride (40g, 0.3 mole). ?'he mixture was heated a t SO0 for 3 hours and thc resulting complex decon~posed and worlccd LIP in the usual manner. The c r~~d e product (18.9 g) was distillcd nncl a fraction, b o i l i~~g a t 140-180' a t 0.2 mm, was collected. This product solidilied slo\vly and was recrystallized scveral times from absolute ethanol to yield 2,7,9,10-tetmrlzeIhyla?rlhrace?1e, m.p. [124][125] 92.74; FI, 7.61 2,7,D, Chromic acitl (1.2 g) \\.as dissolved in the n~inimum amount of water and this solution aclded slowly to 2,i,!J,l0-tetramcthylanthracene (0.74g) dissolved in glacial acetic acid (10 1111). The mixture was heatecl u~~t l e r reflux for 40 millutes and then poured into water (40 ml). 'The r e s u l t i~~g precipitate was collected, partially purihetl by boiling in 5% sodium hytlroxide solution, and recollected. Recrystallization fro111 absolutc ethanol gave 2,7-dimethylanthraquinone as coIorless neetlles (0.55 g), 1n.p. 165-169'; no melting point tlepressio~l \vith a n authentic syrlthetic sample. (;rateful a c l ; n o~-l e d g m e n t is rllacle of t h e f i n a n c i a l a s s i s t a n c e p r o v ? I'rcsetzt (1ddi.e.7~: Sk~trford Resenrcli fttstitute, ilfeizlo P a r k , C(~lifor?rin. Can. J. Chem. Downloaded from www.nrcresearchpress.com by 54.213.91.117 on 05/09/18
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Sy7zthesis of 2,7-IIiirzetlzyln?ztli.rnq71iito1ze 2 , / t , 4 ' -T r i~i z e t l~y I b c t 1~u pFor personal use only.