7-(Benzyloxy)naphthalen-2-ol → Binol

HRID 859089Notes

Reaction equation

HRID 859089 reaction equation
C(O[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([OH:19])=[CH:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C1C2C(=CC=CC=2)C=CC=1O.C(Cl)(Cl)(Cl)Cl>[CH:10]1[CH:11]=[C:12]2[CH:13]=[CH:14][C:15]([OH:19])=[C:16]([C:16]3[C:17]4[C:12](=[CH:11][CH:10]=[CH:9][CH:18]=4)[CH:13]=[CH:14][C:15]=3[OH:19])[C:17]2=[CH:18][CH:9]=1

Participants

4

Reactant 1

HCID 27638187-(Benzyloxy)naphthalen-2-ol

Product 1

HCID 11762BinolYield 80%

Reagents, catalysts & solvents 2

HCID 86632-NaphtholCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A reaction flask described in example 9 was charged with a solution of catalyst 1c (12.2 mg, 0.02 mmol) in anhydrous CCl4 (1 mL). The solution was stirred for 10 min under an oxygen atmosphere and then treated with a solution of 7-benzyloxy-2-naphthol (50 mg, 0.2 mmol) in anhydrous CCl4 (1 mL) under 0° C. The reaction mixture was stirred at 0° C. until the reaction was complete (monitored by TLC). The crude mixture was concentrated under reduced pressure, and purified by column chromatography (Ethyl acetate/Petroleum ether=⅓) to give (R)-BINOL 3g, Yield 80%. [α]D25=−157.4 (c=0.3 in EtOAc), 1HNMR (300 MHz, CDCl3) δ (ppm) 7.89 (d, J=9.0 Hz, 2H, 2×HC (5)), 7.80 (d, J=8.7 Hz, 2H, 2×HC (4)), 7.24 (d, J=9.0 Hz, 2H, 2×HC (3)), 7.10–7.22 (m, 12H, 2×HC (6), 10×PhH), 6.50 (d, J=2.1 Hz, 2H, 2×HC (8)), 5.01 (s, 2H, 2×OH), 4.73.4.84 (m, 4H, 4×OCH2). e.e. 95%.

Workup

  1. customA reaction flask described in example 9
  2. stirringThe reaction mixture was stirred at 0° C. until the reaction
  3. concentrationThe crude mixture was concentrated under reduced pressure
  4. custompurified by column chromatography (Ethyl acetate/Petroleum ether=⅓)

Sources & evidence

ORD record
ord-bb8e13ec745e4b6db71724292b81435d
Source dataset
uspto-grants-2006_12
Patent number
US07151070B2

Reaction notes

Loading…