Uses
(
R)-(+)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-2-naphthol can be used:
- As a starting material for the preparation of octahydro-binaphthyl based organic light-emitting diodes.
- As a ligand in the 1,4-hydrophosphinylation of methyl cyclohexene-1-carboxylate using diphenylphosphine oxide, applicable in the synthesis of CyPHOX ligands.
Synthesis
(R)-1,1'-Bi-2-naphthol (70.52 mM) was used as starting material and added sequentially to an autoclave with platinum oxide (1.15 mM) and acetic acid (25 mL). The reaction was stirred at room temperature for 3 days in a hydrogen atmosphere of 6.8 atm. Upon completion of the reaction, the reaction was quenched by addition of water and dichloromethane. The reaction mixture was extracted three times with dichloromethane and the organic phases were combined. The organic phase was sequentially washed once with water and twice with saturated aqueous sodium bicarbonate and then dried with anhydrous sodium sulfate. After drying, the desiccant was removed by filtration and the filtrate was concentrated to afford the target product 5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol (70.74 mM, quantitative yield). The specific optical rotation of the product was [α]D26 +47.1 (c 1.04, CHCl3).1H NMR (400 MHz, CDCl3) δ= 7.06 (d, 2H, J = 8.2 Hz), 6.82 (d, 2H, J = 8.2 Hz), 4.60 (s, 2H), 2.75 (t, 4H, J = 6.2 Hz), 2.33- 2.25 (m, 2H), 2.19-2.12 (m, 2H), 1.77-1.64 (m, 8H).13C NMR (100 MHz, CDCl3) δ= 151.35, 137.12, 131.01, 130.08, 118.81, 112.93, 29.20, 27.08, 22.98, 22.92 .
References
[1] Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 3220 - 3221
[2] Patent: EP1623971, 2006, A1. Location in patent: Page/Page column 28
[3] Molecules, 2018, vol. 23, # 9,
[4] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 10291 - 10293
[5] Chemistry - A European Journal, 2010, vol. 16, # 44, p. 13116 - 13126
