32565-33-6

Upstream product

• 2284-30-2 4-benzylresorcinol 
• 77-78-1 dimethyl sulfate 
• 100-51-6 benzyl alcohol 
• 151-10-0 1,3-Dimethoxybenzene 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 140-11-4 Benzyl acetate 
• 100-46-9 benzylamine 
• 133730-34-4 2,4-dimethoxyphenylboronic acid 
• 108-46-3 recorcinol 
• 882980-43-0 2-benzyloxy-1-methylpyridinium triflate 
• 120-51-4 benzoic acid benzyl ester 
• 588-46-5 N-(phenylmethyl)acetamide 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 36893-50-2 2,4-dimethoxy-benzophenone-(2,4-dinitro-phenylhydrazone) 
• 60539-15-3 4-(5-benzyl-2,4-dimethoxy-phenyl)-4-oxo-butyric acid 
• 1271737-08-6 5-benzyl-2-hydroxy-2,5-cyclohexadiene-1,4-dione 
• 2284-30-2 4-benzylresorcinol 

Relevant academic research and scientific papers

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions

Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.

SN1 reactions in supercritical carbon dioxide in the presence of alcohols: The role of preferential solvation

Ethanol (3b) inhibits SN1 reactions of alkyl halides 1 in supercritical carbon dioxide (scCO2) and gives no ethers as products. The unexpected behaviour of alcohols 3 in the reaction of alkyl halides 1 with 1,3-dimethoxybenzene (2) in scCO2 under different conditions is rationalised in terms of Br?nsted and Lewis acid-base equilibria of reagents, intermediates, additives and products in a singular solvent characterised by: (i) the strong quadrupole and Lewis acid character of carbon dioxide, which hinders SN2 paths by strongly solvating basic solutes; (ii) the weak Lewis base character of carbon dioxide, which prevents it from behaving as a proton sink; (iii) the compressible nature of scCO2, which enhances the impact of preferential solvation on carbon dioxide availability for the solvent-demanding rate determining step.

Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility

Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct C-C bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.

Supercritical carbon dioxide: A promoter of carbon-halogen bond heterolysis

Amazing reaction medium: Supercritical carbon dioxide, with zero dipole moment, lower dielectric constant than pentane, and non-hydrogen-bonding behavior, ionizes carbon-halogen bonds, dissociates the resulting ion pairs, and escapes from capture by the carbocation intermediates at temperatures above 40 °C. These properties allow the observation of carbocation chemistry in the absence of acids.

Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophage-like RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E2 (PGE2). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for hsPLA2, surface plasmon resonance (SPR) experiments were performed.

Thermally generated phenylcarbenium ions: acid-free and self-quenching Friedel-Crafts reactions

2-Benzyloxy-1-methylpyridinium triflate (1) serves as a stable precursor to a phenylcarbenium species as evidenced by its reactivity in Friedel-Crafts alkylations with electron-rich arenes.

A convenient and improved montmorillonite K-10 catalysed Friedel-Crafts benzylation and allylation with activated esters

Benzyl benzoate and cinnamyl acetate has been effectively used respectively as alkylating and allylating substrates in Friedel-Crafts reaction catalysed by montmorillonite K-10 clay.

Gallium Dichloride-Mediated Reductive Friedel-Crafts Reaction

In the presence of gallium dichloride, the reaction of carbonyl compounds or their dimethylacetals with aromatic compounds afforded Friedel-Crafts alkylated adducts in good yields.It was suggested that the adducts were obtained by way of a reduction of the carbonyl compounds or their dimethylacetals, followed by the Friedel-Crafts reaction in one-pot.This is the first organic synthetic method with gallium dichloride, low valent gallium.