反应详情

Then 97.8 g of that product was combined with 81.9 g of N-bromosuccinimide and 4.2 g of α,α-azo bis isobutyronitrile in 300 ml of carbon tetrachloride and then heated under reflux for 8 hours. The resulting product is filtered off from the succinimide. Then after the solvent is removed in a vacuum, a pale yellow solid was obtained which was determined to be 2-bromomethyl-1-phenylnapthalene was heated with 23 g of calcium carbonate in a mixture consisting of 250 ml of an equal volume mixture of water and dioxane for 10 hours under reflux. The reaction mixture was carefully poured into diluted hydrochloric acid and then extracted with ether and dried and freed of solvent. The resulting product, 2-hydroxymethyl-1-phenylnaphthalene, in an amount of about 0.45 mol was dissolved in 200 ml of acetone and added dropwise to a hot suspension of 207g of KMnO4, 280 ml of water, and 1000 ml of acetone. The suspension was poured into a large glass beaker containing 1000 ml of water to dissolve the magnesium dioxide by the portion-wise addition of dilute HCl and Na2SO3. The product 1-phenylnaphthalene-2-carboxylic acid was isolated by extraction with ether together with extraction of the organic phase with aqueous carbonate solution. This carboxylic acid product was then reacted with polyphosphoric acid. Specifically, 250 g of polyphorphoric acid was heated to 100°-120° C. in a 1000 ml flask. Then 23.9 g of the 1-phenylnaphthalene-2-carboxylic acid was added in portions and the mixture allowed to stand for 1 hour at that temperature. The mixture was then allowed to cool and diluted to 750 ml by the careful addition of ice water. The sticky crude product was extracted with hot toluene and washed with warm aqueous sodium bicarbonate solution. The organic phase was dried and filtered over silica gel. In a cooling cabinet, dark red crystals of the benzo(c) fluorenone separated from the deep red solution.

1. temperatureheated
2. temperatureunder reflux for 8 hours
3. filtrationThe resulting product is filtered off from the succinimide
4. customThen after the solvent is removed in a vacuum
5. customa pale yellow solid was obtained which
6. temperatureunder reflux
7. extractionextracted with ether
8. customdried
9. dissolutionThe resulting product, 2-hydroxymethyl-1-phenylnaphthalene, in an amount of about 0.45 mol was dissolved in 200 ml of acetone
10. additionadded dropwise to a hot suspension of 207g of KMnO4, 280 ml of water, and 1000 ml of acetone
11. additionThe suspension was poured into a large glass beaker
12. additioncontaining 1000 ml of water
13. dissolutionto dissolve the magnesium dioxide
14. additionby the portion-wise addition of dilute HCl and Na2SO3