12-Methyl-1,2,3,4-tetrahydrochrysene → 6-Methylchrysene

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A mixture of palladium on carbon (10%, 5.0 g) and 6-methyl-7,8,9,10-tetrahydro-chrysene (64.0 g, 0.24 mol) in triglyme (290 mL) was heated at 210° C. under a slow nitrogen stream. The progress of the reaction was monitored by NMR analysis that showed the reaction was 72% complete after 4 hours. The heating was discontinued after 18 hours when essentially all of the starting material had been consumed. The mixture was cooled to 100° C. and filtered to remove the catalyst. The solution was then cooled further to 0° C., and filtered to give 42.9 g (68% yield) of 6-methylchrysene. The filtrate was diluted with water (300 mL) and filtered to give an additional 15.5 g (93% combined yield) of 6-methylchrysene. 1H NMR (CDCl3) 2.86 (s, 3 H), 7.6 (m, 4 H), 7.9 (m, 2 H), 8.1 (m, 1 H), 8.55 (s, 1 H), 8.65 (m, 1 H), 8.8 (m, 2 H).

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