Ethyl Acetate → 2-Naphthol

HRID 859087Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:7][CH:8]([OH:10])[CH3:9].[CH3:11]COC(C)=O>>[CH:7]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:1]=2)[CH:11]=[CH:9][C:8]=1[OH:10]

Participants

Reactant 2

HCID 8857Ethyl Acetate

HCID 21585144Isopropanol hexane

Product 1

HCID 86632-Naphthol

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 6-bromo-2-naphthol (44 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 3c, Yield 99%. [α]D25=−33.7 (c=0.4 in EtOAc), 1H NMR (300 MHz, CDCl3) δ (ppm) 8.06 (d, J=1.8 Hz, 2H, 2×HC (4)), 7.89 (d, J=9.0 Hz, 2H, 2×HC (5)), 7.37 (d, J=6.9 Hz, 2H, 2×HC (8)), 7.36 (dd, J=9.0 Hz, 1.8 Hz, 2H, 2×HC (7)), 6.96 (d, J=9.0 Hz, 2H, 2×HC (3)), 5.08 (s, 2H, 2×OH). e.e. 90%, and the configuration was R (Kromasil CHI-TBB column, Hexane/propan-2-ol=80: 20; flow rate 1 mL/min; S-isomer, tR 6.68 min and R-isomer, tR 7.51 min).

Sources & evidence

ORD record: ord-849c507115774603a41d09b7fb183da8
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151070B2

Reaction notes

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