[1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,602-09-5
To 18.3 g of sodium hydride was added 50 g (0.175 mol) of 2,2′-dihydroxy-1,1′-dinaphthyl and stirred under nitrogen in 1.0 L of dry tetrahydrofuran (THF). After 1 hour, 116 g of chloromethyl methyl ether was added to the heavy precipitate and the resulting mixture was stirred for about 12 hours and then filtered through a pad of celite. The filtrate was shaken with 500 ml of water and 1 L of methylene chloride. An aqueous layer formed and was extracted two times more with methylene chloride. The combined organic layers were washed with water saturated with potassium bicarbonate. The organic layer was dried and filtered through a squat column of alumina and the column filtrate was evaporated until crystals appeared. The crude product was purified on a silica gel column by elution with a methylene chloride/hexane solution. About 53.5 g (63%) of 2,2′-bis(methoxymethoxy)-1,1′-dinaphthyl, m.p 93-94 C., 0.11 mol was collected. [00053] Next, 171 ml of 1.6 N butyllithium in hexane was added to a mixture of 41 g of the above bisacetal in 1 L of tetrahydrofuran and stirred under nitrogen at 0 C. for 45 minutes. The reaction mixture was then allowed to warm to 25 C. and 25.8 ml of dimethyl sulfate was added to the suspension and the mixture was stirred for 12 hours. About 30 ml of water saturated with sodium carbonate was added and the solvent was evaporated under reduced pressure at 50 C. [00054] The residue, in 300 ml of methylene chloride, was washed twice with water. An additional 300 ml of methylene chloride, 300 ml of methanol, and 25 ml of concentrated hydrochloric acid was added to the organic solution. The solution was stirred for 3 hours, and the solvent was evaporated. The yellow product was recrystallized from methylene chloride-hexane and was purified on a silica gel column (methylene chloride, hexane 1:1) to give 29.5 g (86%) of (R)-3-3′-dimethyl-2,2′-dihydroxy-1,1′-dinaphthyl, m.p. 204-206 C.; 1HNMR:2.2(s.6H), 7.1(d.2H), 7.3(m.2H), 7.4(m.2H), 7.8(m.4H).
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Reference£º
Patent; IBC Advanced Technologies, Inc.; US6686479; (2004); B2;,
Chiral Catalysts
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