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- W2185564223 abstract "[79547-82-3] C21H16O2 (MW 300.36)InChI = 1S/C21H16O2/c1-23-19-13-11-15-7-3-5-9-17(15)21(19)20-16-8-4-2-6-14(16)10-12-18(20)22/h2-13,22H,1H3InChIKey = SYSSVMYYSHYMAQ-UHFFFAOYSA-N(reagent used as chiral proton source or chiral ligand in several enantioselective reactions)Physical Data: mp 89–91 °C; [α]D27 +38.9 [c 0.68, THF, 99.3% ee (R)], [α]D28 −44.8 (c 1.4, CHCl3, 99.3% ee (R)]; HPLC [CHIRALCEL OD, 5% i-PrOH–hexane, retention time for the (R)-enantiomer, 25.12 min; for the (S)-enantiomer, 35.47 min]; IR (Nujol) 3478 cm−1; 1H NMR (300 MHz, CDCl3) δ3.81 (s, 3H), 4.91 (s, 1H, exchangeable with D2O), 7.04 (br d, 1H, J = 7.7 Hz), 7.14–7.40 (m, 6H), 7.49 (d, 1H, J = 9.3 Hz), 7.86 (br d, 1H, J = 8.0 Hz), 7.90 (d, 2H, J = 8.5 Hz), 8.06 (d, 1H, J = 9.1 Hz); MS m/z = 300 (M+, 100%).Solubility: soluble in alcohol, diethyl ether, toluene, and most organic solvents.Form Supplied in: white solid.Preparative Methods: (R)-2-hydroxy-2′-methoxy-1,1′-binaphthyl [(R)-BINOL-Me] can be prepared from commercially available (R)-1,1′-bi-2-naphthol [(R)-BINOL] by the use of 1 mol equiv of methyl iodide and sodium hydride in N,N-dimethylformamide (DMF)1a or by the use of Mitsunobu reaction.1bPurification: recrystallization from toluene–hexane or purification by silica gel column chromatography from a hexane– AcOEt (8:1) eluent.Handling, Storage, and Precautions: very stable in air." @default.
- W2185564223 created "2016-06-24" @default.
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- W2185564223 date "2013-09-16" @default.
- W2185564223 modified "2023-09-25" @default.
- W2185564223 title "(R)-2-Hydroxy-2′-methoxy-1,1′-binaphthyl" @default.
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- W2185564223 doi "https://doi.org/10.1002/047084289x.rn00119.pub2" @default.
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