73453-80-2

Upstream product

• 73453-77-7 3-(4,4-dimethyloxazolin 2-yl)anisole 
• 66-99-9 β-naphthaldehyde 
• 586-38-9 3-Methoxybenzoic acid 
• 73453-79-9 4-Methoxy-3-(2-naphthyl)phthalide 

Downstream Products

• 62064-44-2 8-Hydroxy-7,12-dimethylbenzanthracene 
• 73453-81-3 3-Methoxy-2-(2-naphthylmethyl)benzoic Acid 

Relevant academic research and scientific papers

Synthesis of 8-Hydroxy- and 11-Hydroxy-7,12-dimethylbenzanthracenes. Tin(II) Chloride Mediated Reductions

8-Methoxybenzanthracene-7,12-dione (3) and 11-methoxybenzanthracene-7,12-dione (4) were converted in high yields to the corresponding 7,12-bis(epoxides) (14a and 14b) (not isolated because of instability) by treatment with the ylide formed from trimethylsulfonium iodide.Reduction with lithium aluminium hydride afforded 7,12-dihydro-7,12-dihydroxy-8-methoxy-7,12-dimethylbenzanthracene (5) and 7,12-dihydro-7,12-dihydroxy-11-methoxy-7,12-dimethylbenzanthracene (6), respectively, in excellent yields.Treatment of 5 and 6 with stannous chloride and hydrogen chloride (or hydrochloric acid) in ether, ethyl acetate, dioxane, and tetrahydrofuran gave over 90percent yields of 8-methoxy-7,12-dimethylbenzanthracene (1) and 11-methoxy-7,12-dimethylbenzanthracene (2), respectively.A discussion of the mechanism of these reductions focuses on the formation of an organotin intermediate and not a free carbenium ion.