66595-77-5

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 135-19-3 β-naphthol 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 

Downstream Products

• 37097-20-4 14-(4-chlorophenyl)-14H-dibenzo[a,j]xanthene 
• 66596-18-7 bis-(2-acetoxy-[1]naphthyl)-(4-chloro-phenyl)-methane 

Relevant academic research and scientific papers

Novel and potent Lewis acid catalyst: Br2-catalyzed Friedel-Crafts reactions of naphthols with aldehydes

A discovery that the inexpensive Br2 can serve as a potent Lewis acid catalyst for bis(2-hydroxy-1-naphthyl)methanes synthesis is presented. Under the catalysis of Br2 at room temperature, naphthols reacted smoothly with various aldehydes with high efficiency and broad substrate scope. This reaction used to require highly acidic conditions and/or high temperature and/or pressure, and sometimes featured poor yields. Moreover, theoretical calculations suggested that Br2 is a potent Lewis acid to activate the carbonyl group, yet it was not the primary cause for the remarkable activity of Br2 in the current communication.

Ionic Liquid [DABCO-H][HSO4] as a Highly Efficient and Recyclable Catalyst for Friedel-Crafts Alkylation in the Synthesis of Bis(naphthol)methane and Bis(indolyl)methane Derivatives

A simple and highly efficient approach to the synthesis of bis(naphthol)methane (BNM) and bis(indolyl)methane (BIM) derivatives has been developed. In the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO)-based ionic liquid catalysts, which are environmental friendly, inexpensive, and recyclable, the reaction afforded the corresponding products in good to excellent yields within short times under solvent-free conditions. The catalysts can be easily recovered and reused several times without significant loss in activity.

N-Sulfonic acid poly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst for one-pot synthesis of xanthene derivatives in dry media under ultrasound irradiation

N-Sulfonic acid poly(4-vinylpyridinium) hydrogen sulfate catalyzed efficiently the synthesis of xanthene derivatives under ultrasonic irradiation at room temperature, which has prompted various concerns involving cost and environmental persistence. This methodology shows the effect of presence of anion hydrogen sulfate as an important and effective factor on the promotion of the one-pot multi-components and condensation reactions. The catalyst can be recovered by simple filtration and used for several times without a significant loss of catalytic activity.

Investigation of keto-enol tautomers during the synthesis of aryl-bis (2-hydroxy-1-naphthyl)methanes

This study investigated the existence of keto-enol tautomers for the first time during the synthesis of aryl-bis(2-hydroxy-1-naphthyl)methane from 2-naphthol and p-tolualdehyde or 4-chlorobenzaldehyde in methanol using CuSO4.5H2O as catalyst under reflux condition. The exclusive formation of aryl-bis(2-hydroxy-1-naphthyl)methanes was observed in dichloromethane at room temperature in the presence of BF3.OEt2/AcOH as catalyst. The keto products were isolated and characterized by 1H NMR, 13C NMR, COSY and DEPT spectra. [Figure not available: see fulltext.]

Hydrobromic acid-catalyzed Friedel-Crafts type reactions of naphthols

Catalyzed by 10 mol% of hydrobromic acid, hydroxyalkylation and allylation-iodocyclization of naphthols proceeded smoothly under mild conditions. In contrast, other Bronsted acids tested, including HCl, HI, HBF4, HPF6, TFA, PTSA, H2SO4, TfOH etc., are almost ineffective under identical conditions or require harsh reaction conditions.

1,3-Dibromo-5,5-dimethylhydantoin (DBH)/kaolin: An efficient reagent system for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions

1,3-Dibromo-5,5-dimethylhydantoin, has been used as an efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes in the presence of kaolin. All reactions are performed in the absence of solvent in relatively short reaction times in good to

Green and diasteroselective oxidative cyclization of bisnaphthols to spirans

Hydrogen peroxide/MoO3, as an efficient and clean oxidizing system was used to afford diasteroselective oxidative cyclization of bisnaphthols to spirans in ethanol at 60 °C with high yields. Bisnaphthols were prepared by the reaction of a series of aldehydes and 2-naphthol in the presence of a catalytic amount of H3[P(Mo3O 10)4].nH2O (HPA) in refluxing dichloromethane.

A simple and efficient method for the synthesis of amidophenols using iodine as catalyst under neat condition

A convenient and efficient one-pot synthesis of substituted amidophenols using iodine as catalyst at room temperature under neat condition is described.

Yb(OTf)3 catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: a green synthesis of aryl-14H-dibenzo[a,j]xanthenes

A facile, efficient and green synthesis of aryl-14H-dibenzo[a,j]xanthenes has been developed by one-pot condensation of β-naphthol and substituted benzaldehydes in the presence of ytterbium triflates in ionic liquids.

High-yielding TfOH-catalyzed condensation of phenols with aromatic aldehydes at high pressure. A model synthesis of the benzylidene biphenol key skeleton of blepharismins

An approach to the benzylidene biphenol key component of blepharismins, photoreceptor pigments isolated from Blepharisma japonicum, is reported. This method relies on an efficient TfOH-catalyzed condensation of phenols with aromatic aldehydes in EtOH as a solvent at 3 kbar pressure.