2-Naphthol → Binol

HRID 859094Notes

Reaction equation

HRID 859094 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11]>C1C2C(=CC=CC=2)C=CC=1O.C(Cl)(Cl)(Cl)Cl>[CH:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][C:2]([OH:11])=[C:1]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][C:2]=3[OH:11])[C:10]2=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 86632-Naphthol

Product 1

HCID 11762BinolYield 85%

Reagents, catalysts & solvents 2

HCID 86632-NaphtholCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A two-neck round bottom flask (50 mL) was charged with a solution of catalyst 1c (122 mg, 0.2 mmol) in anhydrous CCl4 (10 mL). The solution was stirred for 10 min under an oxygen atmosphere and then treated with a solution of 2-naphthol (290 mg, 2 mmol) in anhydrous CCl4 (10 mL). 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 3a, Yield 85%. 1HNMR (300 MHz, CDCl3) δ (ppm) 7.98 (d, J=9.0 Hz, 2H, 2×HC (4)), 7.90 (d, J=7.8 Hz, 2H, 2×HC (5)), 7.38 (d, J=9.0 Hz, 2H, 2×HC (8)), 7.41–7.27 (m, 4H, 2×HC (6), 2×HC (7)), 7.16 (d,J=8.4 Hz, 2H, 2×HC (3)), 5.09 (s, 2H, 2×OH). e.e. 90% and the configuration was R (Kromasil CHI-TBB column, Hexane/propan-2-ol=90: 10; flow rate 1 mL/min; S-isomer, tR 7.78 min and R-isomer, tR 8.79 min).

Workup

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

Sources & evidence

ORD record
ord-b9b1e717cd214d569cf38833b78fd17f
Source dataset
uspto-grants-2006_12
Patent number
US07151070B2

Reaction notes

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