3098-18-8

Usage

Preparation

Preparation by Friedel–Crafts acylation of m-cresol, ? with benzoic acid in the presence of boron trifluoride at 160° for 2 h (94%) or in the presence of Amberlyst-15 in refluxing chlorobenzene for 65 h (37%) ; ? with benzoyl chloride in the presence of aluminium chloride at 75°, in nitrobenzene at 60° for 18 h (8%) or with titanium tetrachloride in the same conditions (17%).

InChI:InChI=1/C14H12O2/c1-10-7-8-12(13(15)9-10)14(16)11-5-3-2-4-6-11/h2-9,15H,1H3

Upstream product

• 614-32-4 3-methylphenyl benzoate 
• 4072-11-1 2-methoxy-4-methyl-benzophenone 
• 4937-62-6 2-amino-4-methylbenzophenone 
• 108-39-4 3-methyl-phenol 
• 98-07-7 Benzotrichlorid 
• 65-85-0 benzoic acid 
• 10425-07-7 4-hydroxy-2-methylbenzophenone 
• 98-88-4 benzoyl chloride 
• 698-27-1 4-methylsalicylaldehyde 
• 98-80-6 phenylboronic acid 
• 74993-52-5 O-(3-methylphenyl)hydroxylamine 
• 937716-84-2 N-(3-methyl)phenoxyphthalimide 
• 17933-03-8 m-tolylboronic acid 
• 1443440-55-8 N-(m-tolyloxy)acetamide 

Downstream Products

• 50-85-1 2-hydroxy-p-toluic acid 
• 30091-04-4 2-Benzyl-5-methyl-phenol 
• 4072-11-1 2-methoxy-4-methyl-benzophenone 
• 1025506-16-4 4-phenyl-7-methyl-1,2,3-benzoxathiazine 2,2-dioxide 
• 1334247-32-3 (S)-2-(amino(phenyl)methyl)-5-methylphenol 
• 1334335-00-0 2-(imino(phenyl)methyl)-5-methylphenol 
• 1279131-20-2 (S)-5-methyl-2-(phenyl((3,4,5-trimethoxyphenyl)amino)methyl)phenol 
• 1279130-97-0 (E)-5-methyl-2-(phenyl((3,4,5-trimethoxyphenyl)imino)methyl)phenol 
• 854843-65-5 8-benzyl-2,5-dimethyl-chromen-4-one 
• 614-32-4 3-methylphenyl benzoate 
• 10425-07-7 4-hydroxy-2-methylbenzophenone 
• 108-39-4 3-methyl-phenol 
• 137937-47-4 (2-hydroxy-4-methylphenyl)(phenyl)methanone benzoate 
• 137956-29-7 4-hydroxy-2-methylbenzophenone benzoate 

Relevant academic research and scientific papers

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

RhIII-Catalyzed Decarboxylative o-Acylation of Arenes Bearing an Oxidizing Directing Group

Here in we report, rhodium(III)-catalyzed decarboxylative acylation of arenes using α-oxocarboxylic acids as acyl surrogate. In this strategy, O–NHAc group act as an autocleavable oxidizing directing group (ODGauto), thus giving rise to ortho-acylated phenols in moderate to good yields. Mechanistic studies provided strong support for a kinetically relevant C–H bond activation. According to the best of our knowledge, this is the first report of Rhodium catalyzed decarboxylative acylation.

Series of high spin mononuclear iron(III) complexes with Schiff base ligands derived from 2-hydroxybenzophenones

The reaction of various phenols with benzoyl chloride afforded the derivatives of phenyl benzoate that subsequently underwent Fries rearrangement. The obtained 2-hydroxybenzophenone analogues were combined with linear aliphatic triamines, which afforded pentadentate Schiff base ligands. Moreover, nine new iron(iii) complexes with the general formula [Fe(Ln)X] (where, Ln is the dianion of the pentadentate Schiff base ligand, N,N′-bis((2-hydroxy-5-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L1, N,N′-bis((2-hydroxy-3,5-dimethylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L2, N,N′-bis((2-hydroxy-5-chlorophenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L3, N,N′-bis((2-hydroxy-4-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L4, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-azaheptane = H2L5, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-methyl-4-azaheptane = H2L6 and X is the chlorido, azido or isocyanato terminal ligand) were synthesized and characterized via elemental analysis, and IR and UV-VIS spectroscopy; in addition, the crystal structures of all the complexes were determined by X-ray diffraction. Magnetic investigation reveals high spin state behaviour in all the reported compounds. DFT calculations and analysis of the magnetic functions allowed to extract absolute values of the zero field splitting parameters and exchange coupling constants.

Efficient microwave-assisted direct C-benzoylation of phenols and naphthols with benzoic acid catalyzed by bismuth triflate under solvent-free or ionic liquid conditions

An efficient and simple route for the synthesis of ortho-hydroxyaryl ketones has been developed. The microwave-assisted direct C-benzoylation of phenols and naphthols in the presence of metal triflates afforded the corresponding ortho-hydroxyaryl ketones in moderate to excellent yields. Bismuth triflate showed the best catalytic performance compared to other metal triflates. The protocol has advantages including short reaction times, high chemoselectivity towards C-acylation, and simple work-up. Additionally, bismuth triflate can be easily recovered and reused several times without significant loss of catalytic performance.

Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: Effective synthesis of optically active homotyrosines

Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.

Enantioselective synthesis of cyclic sulfamidates via Pd-catalyzed hydrogenation

Using Pd(CF3;CO2)2/(S,S)-f-binaphane as the catalyst, an efficient enantioselective synthesis of cyclic sulfamidates was developed via asymmetric hydrogenation of the corresponding cyclic imines in 2,2,2-trifluoroethanol at room temperature with high enantioselectivities (up to 99% ee).

Direct acylation of phenol and naphthol derivatives in a mixture of graphite and methanesulfonic acid

Graphite in methanesulfonic acid is used to prepare o-hydroxyketones by direct acylation of phenol and naphthol derivatives with carboxylic acids. Georg Thieme Verlag Stuttgart.

Improvement of Selectivity in the Fries Rearrangement and Direct Acylation Reactions by Means of P2O5/SiO2 Under Microwave Irradiation in Solvent-Free Media

P2O5/SiO2 was found to be an efficient new reagent for the Fries rearrangement of acyloxy benzene or naphthalene derivatives and the direct acylation reactions of phenol and naphthol derivatives with carboxylic acids. The reactions proceeded smoothly in the solid state and are highly selective methods for the preparation of the ortho isomers of hydroxyaryl ketones. Microwave irradiation improved the conversion yield to 85-100 percent and the high ortho-regioselectivity of these reactions provides an efficient and versatile procedure for obtaining o-hydroxyaryl ketones in 47-98 percent yield.

Hypolipidemic 1,4-benzothiazepine derivative

The invention is concerned with a novel hypolipidemic compound, which is of (3R,5R)-3-Butyl-3-ethyl-2,3,4,5-tetrahydro-7-methoxy-5-phenyl-1,4-benzothiazepin-8-ol 1,1-dioxide; or a salt, solvate, or physiologically functional derivative thereof, with processes for its preparation, pharmaceutical compositions containing it and with its use in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions, such as athersclerosis.

Sandmeyer reactions. Part 5.1 Estimation of the rates of 1,5-aryl/aryl radical translocation and cyclisation during Pschorr fluorenone synthesis with a comparative analysis of reaction energetics

During the Pschorr cyclisation of 2-aroylphenyl radicals, a rearrangement occurs reversibly by 1,5-hydrogen transfer to give 2-benzoylaryl radicals. Rate constants of (1.2 ± 0.2) × 106 s-1 at 293 K are estimated for both the forward and back reactions in the equilibrium between 2-(4-methylbenzoyl)phenyl and 2-benzoyl-5-methylphenyl radicals. Assuming an empirical estimate of 1.6 × 10-2 dm3 mol-1 s-1 for the hypothetical rate of abstraction of hydrogen from benzene by phenyl radicals, the radical translocation is calculated to occur with a statistically corrected effective molarity of 2.2 × 108 mol dm-3. By contrast, the competing cyclisation, though occurring at a rate of (8.0 ± 0.9) × 105 s-1, exhibits an effective molarity of only 5.3 mol dm-3. The causes of these differences are analysed in terms of reaction mechanism.