ChemicalBook CAS DataBase List 1,1'-Bi-2-naphthol

1,1'-Bi-2-naphthol synthesis

9synthesis methods

Product Name:1,1'-Bi-2-naphthol
CAS Number:602-09-5
Molecular formula:C20H14O2
Molecular Weight:286.32

A process for coupling 2-naphthols which comprises contacting a 2-naphthol dissolved in a polar acidic organic solvent in the presence of a catalytic amount of a catalyst which comprises a readily reducible form of a Group IB, Group VIII or manganese metal in the further presence of oxygen or a source of oxygen at a temperature between 0° and 200° C. under conditions such that a 1,1'-bi-2-naphthol is prepared wherein the product contains less than about 1 mole percent of binaphthenoquinones.

135-19-3 Synthesis

135-19-3
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$9.00/1g

602-09-5
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$6.00/5g

Yield:602-09-5 99.3%

Reaction Conditions:

with manganese dioxide in acetonitrile at 25; under 760.051 Torr;

Steps:

2.2 The Synthesis of1,1′-bi-2-naphthols

General procedure: For the synthesis of 1,1′-bi-2-naphthols, 0.1g MnO2powderwas added into 40mL of 25mm 2-naphthols acetonitrile ortoluene solution. Due to the toxicity of toluene solvent andsame synthetic effect (see Fig. S2), our investigations weremainly conducted in 2-naphthols acetonitrile solution. Thesynthesis reaction was performed at atmospheric pressureand room temperature, and the MnO2powder was continuouslystirred. For the sake of comparison, the 2-naphtholssolution/MnO2 powder reaction system was put in dark andvisible-light irradiation condition, respectively. In addition,2-naphthol solution/P25(TiO2) powder reaction system and2-naphthol solution/BiVO4 powder reaction system weresimilarly treated. As the reaction time increased, the 2-naphtholacetonitrile solution gradually changed from colorlessinto brown. To detect the formation of 1,1′-bi-2-naphthols,the resultant solution was analyzed by liquid chromatography(LC-16, Shimadzu) and liquid chromatography-massspectrometry (LCMS-8040, Shimadzu), respectively. Thedetection wavelength of liquid chromatography was 280nm,and the volume ratio of mobile phase was 70% methanol-H2O. Before the detection of 1H and 13C NMR spectroscopy(JEOL Eclipse 400), the 1,1′-bi-2-naphthols product waspurified by SiO2gel thin plate using ethyl acetate/hexane(4:6) as an unfolding agent. In addition, for the 2-naphthol/-MnO2 powder system, the dissolved Mn in the reaction solutionafter 12h was detected by inductively coupled plasmamass spectrometry (ICP-MS, Thermo ICAP6300).

References:

Wu, Yuting;Yang, Long;Wu, Bo;Li, Jie;Liu, Binyao;Ke, Gaili;Dong, Faqin;Zhou, Yong;He, Huichao [Catalysis Letters,2021,vol. 151,# 3,p. 901 - 908]

573-97-7 Synthesis