10425-05-5

Usage

Preparation

Preparation by Fries rearrangement of p-tertbutylphenyl benzoate with, ? titanium tetrachloride without solvent at 140° for 15 min (47%) or in nitromethane at r.t. for 7 days (29%) ; ? aluminium chloride without solvent at 180° for 15 min (35%).

InChI:InChI=1/C17H18O2/c1-17(2,3)13-9-10-15(18)14(11-13)16(19)12-7-5-4-6-8-12/h4-11,18H,1-3H3

Upstream product

• 98-54-4 para-tert-butylphenol 
• 98-07-7 Benzotrichlorid 
• 14041-81-7 4-tert-butylphenyl benzoate 
• 100-47-0 benzonitrile 
• 65-85-0 benzoic acid 
• 75846-32-1 5-(tert-butyl)-3-phenylbenzofuran-2(3H)-one 
• 611-71-2 MANDELIC ACID 
• 100-52-7 benzaldehyde 
• 2725-53-3 2-hydroxy-5-t-butylbenzaldehyde 
• 98-80-6 phenylboronic acid 
• 1260403-07-3 4-(tert-butyl)-2-(hydroxy(phenyl)methyl)phenol 
• 108-86-1 bromobenzene 
• 98-88-4 benzoyl chloride 
• 5396-38-3 1-(tert-butyl)-4-methoxybenzene 

Downstream Products

• 112848-92-7 (E)-2-hydroxy-5-t-butylbenzophenone oxime 
• 116285-97-3 (5-tert-Butyl-2-hydroxy-phenyl)-phenyl-methanone oxime 
• 1374329-55-1 3-acetyl-6-tert-butyl-4-phenyl-2H-chromen-2-one 
• 1202634-06-7 5-(tert-butyl)-3-phenylbenzofuran 
• 1393123-09-5 C₁₃H₉⁽¹⁸⁾FO₂ 
• 362-47-0 (5-fluoro-2-hydroxyphenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Synthesis of Aryl Ketones by the Pd-Catalyzed C-H Activation of Arenes and Intermolecular Carbopalladation of Nitriles

The palladium-catalyzed reaction of simple arenes and nitriles provides good to excellent yields of aryl ketones or the corresponding hindered imines. The addition of a small amount of DMSO increases the yields dramatically. Both intermolecular and intramolecular examples of this process are successful. This novel chemistry is believed to involve palladium-catalyzed C?H activation, followed by carbopalladation of the nitrile. Copyright

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?

In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.

Photo-Fries rearrangement in flow under aqueous micellar conditions

A flow edition of photo-Fries rearrangement for the synthesis of 2-acylphenols in an aqueous micellar medium has been described. We take advantage of a narrow channel reactor and micelle-induced confinement effect to refine both the efficiency and selectivity of the parent photoreaction. This journal is

Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones

We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.

Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies

Irradiation of a series of p-substituted aryl benzoates under N2 atmosphere in homogeneous and micellar media was investigated by means of steady-state condition and of time-resolved spectroscopy. A notable selectivity in favor of the 2-hydroxybenzophenone derivatives was observed in micellar media. The benzophenone derivatives were the main photoproduct. On the other hand, in homogeneous media (cyclohexane, acetonitrile, and methanol) the observed product distribution was entirely different, viz. substituted 2-hydroxybenzophenones, p-substituted phenols, benzyl and benzoic acid were found. The binding constants in the surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.

Expanded campestarene hosts for tetra- and dinuclear uranyl(VI) complexes

The first expanded campestarenes based on a keto-enamine scaffold have been constructed using uranyl acetate as a template. Macrocycles with six and eight aryl rings in their backbone host dinuclear and tetranuclear uranium(vi) species, respectively. The complexes were characterized by SCXRD, FT-IR, UV-vis, and NMR spectroscopy, and DFT calculations corroborated their structures.

One-pot synthesis of ortho-acylphenols by palladium-catalyzed phenol C–H addition to nitriles

The regioselective one-pot synthesis of ortho-acylphenols via the palladium-catalyzed addition of phenols to nitriles and subsequent hydrolysis is reported. The acylation reaction proceeded smoothly using the Pd(OAc)2/DMSO system and TFA as the additive. This method also provides a direct strategy for the synthesis of a salicylketoxime scaffold.

Metal-free oxidative fluorination of phenols with [18F]fluoride

The radiochemical synthesis of [18F]4-fluorophenols is based on phenol umpolung under oxidative conditions and direct nucleophilic fluorination with [18F]fluoride (see scheme, TBAF=tetra-n-butylammonium fluoride, TFA=trifluoroacetic acid). Readily available O-unprotected 4-tert-butyl phenols are used as precursors in this one-pot protocol. The reaction is completed in less than 30 minutes at room temperature and can be performed using standard or microfluidic technology. Copyright

One-pot synthesis of 3,4-disubstituted coumarins under catalysis of Mn 3O4 nanoparticles

The one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles was developed. A series of 3,4-disubstituted coumarin derivatives were obtained in good yields. A new method for the one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles has been developed. A series of 3,4-disubstituted coumarin derivatives were synthesized from substituted 2-(hydroxymethyl)phenols and β-keto esters in good yields. Copyright