Background and overview[1]
5,12-Bis(phenylethynyl)tetracene is an organic synthesis intermediate and pharmaceutical intermediate, which can be used in laboratory research and development processes and chemical and pharmaceutical research and development processes.
Preparation[1]
5,12-bis(phenylethynyl)tetracene is prepared as follows:
1) Add 51.0g (0.50 mol) anhydrous dioxane to a suspension of 11.5g (0.50 mol) lithium amide in 600 ml, and heat the mixture to reflux for 2 hours. To the warm mixture was added 52.0 g (0.50 mol) of 9,10-anthraquinone, and the mixture was heated to reflux for 16 hours. The cooled mixture was treated with 1 liter of 0.5M aqueous ammonium chloride solution. The product was filtered off and washed with water. Recrystallization from acetonitrile gave colorless crystals. 220°C (melting point M.P. 206-207), yield 47%.
2) Dissolve 5 grams of 9,10-dihydroxy-9,10-bis(phenylethynyl)9,10-dihydroanthracene in 50 ml of dioxin.
3) Prepare lithium phenylacetylene from 14.85 g (0.146 mol) of phenylacetylene and 2.80 g (0.122 mol) of lithium amide in 100 ml, and then add 15.7 g of 0.25 (0.061) to 150 ml of 0.83 dioxane mol) of 5,12-naphthoquinone and the mixture was refluxed for 4 hours, then cooled and treated with 3.50 ml of 0.5 M aqueous ammonium chloride solution. The product was recrystallized from benzene to obtain 15.95 g (57%) of colorless crystals of 5,12-dihydroxy-5,12-bis(phenylethynyl)-5,12-dihydronaphthocene, M.P. 216.5-218℃ (decomposition).
4) In 200 ml of 29 g of stannous chloride solution, slowly add 14.4 g of 5,12-dihydroxy-5,12-bis-(phenylethynyl)-5,12-di in 50 ml of acetic acid aqueous solution. Hydronaphthalene, incorporated into dioxane. The mixture was stirred at room temperature for 2 hours, then diluted to a volume of 1,500 ml, and the crude product was recrystallized from benzene to obtain 8.1 g (63%) of dark red-purple needle 5,12-bis(phenylacetynyl)tetracene.
Main reference materials
[1] US3557233
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