39531-24-3

Upstream product

• 106-44-5 p-cresol 
• 532-28-5 (RS)-mandelonitrile 
• 65425-11-8 5,5′-dimethyl-3,3′-diphenyl-3H,3′H[3,3′]-bibenzofuranyl-2,2′-dione 
• 22979-35-7 Methyl phenyldiazoacetate 
• 92545-50-1 methyl α-(2-hydroxy-5-methylphenyl)phenylacetate 
• 98416-35-4 N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide 
• 611-71-2 MANDELIC ACID 

Downstream Products

• 14385-52-5 5-methyl-3-phenyl-2,3-benzofuran 
• 111864-86-9 trans-2-methoxy-5-methyl-3-phenyl-2,3-dihydrobenzofuran 
• 111864-86-9 cis-2-methoxy-5-methyl-3-phenyl-2,3-dihydrobenzofuran 
• 1258326-23-6 C₂₅H₁₉NO₄ 
• 1470-57-1 2-hydroxy-5-methylbenzophenone 
• 65425-11-8 5,5′-dimethyl-3,3′-diphenyl-3H,3′H[3,3′]-bibenzofuranyl-2,2′-dione 

Relevant academic research and scientific papers

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.

Recyclable nickel-catalyzed C-H/O-H dual functionalization of phenols with mandelic acids for the synthesis of 3-aryl benzofuran-2(3: H)-ones under solvent-free conditions

Herein, we developed a protocol for the efficient synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions from phenols and mandelic acids using Ni(OTf)2 as a catalyst. A diverse range of mandelic acids and phenols undergo C-H/O-

A benzofuran compound and its efficient catalytic synthesis method

The invention discloses a to trifluoromethanesulfonic acid nickel as catalyst, in order to mandelic acid and phenol as raw materials, and efficient synthesis of the benzofuran compound of the method, this method has the advantages of low cost, high yield,

SbCl3-catalyzed solvent-free Friedel–Crafts reaction of phenols with mandelic acids to 3-aryl benzofuran-2(3H)-ones: Synthesis of spirocyclic 2,3-dihydrobenzofuran-2-ones

A facile, SbCl3-catalyzed, one-pot, tandem Friedel–Crafts/lactonization reaction of phenols and mandelic acids has been developed under solvent-free conditions to afford 3-aryl benzofuran-2(3H)-ones in good to high yields (52–90%). Additionally

Highly site-selective direct C-H bond functionalization of phenols with α-aryl-α-diazoacetates and diazooxindoles via gold catalysis

An unprecedented direct C-H bond functionalization of unprotected phenols with α-aryl α-diazoacetates and diazooxindoles was developed. A tris(2,4-di-tert-butylphenyl) phosphite derived gold complex promoted the highly chemoselective and site-selective C-H bond functionalization of phenols and N-acylanilines with gold-carbene generated from the decomposition of diazo compounds, furnishing the corresponding products in moderate to excellent yields at rt. The salient features of this reaction include readily available starting materials, unprecedented C-H functionalization rather than X-H insertion, good substrate scope, mild conditions, high efficiency, and ease in further transformation. To the best of our knowledge, this is the first example of C-H functionalization of unprotected phenols with diazo compounds.

Unexpected formation of benzofuran derivatives in the C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2-phenylethylidene)benzenesulfonamide

The C-amidoalkylation of p-cresol with 4-chloro-N-(2,2-dichloro-2- phenylethylidene)benzenesulfon-amide in the presence of H2SO 4, oleum, or a mixture of H2SO4 and P 4O10 was studied for the first time. It was shown that the reaction not only leads to the targeted 4-chloro-N-[2,2-dichloro-1-(2-hydroxy- 5-methylphenyl)-2-phenylethyl]benzenesulfonamide but is also accompanied by unexpected formation of the heterocyclic derivatives 4-chloro-N-(5-methyl-2- phenyl-1-benzofuran-3-yl)benzenesulfonamide and 5-methyl-3-phenyl-2-benzofuran- 2(3H)-one.

Some reactions of persistent benzofuranone radicals related to the 'old' diazonamide structure

The benzofuranone dimers 9 and 10/11 readily (ca. 75°C) dissociate to the persistent radicals 16 and 17 respectively, which are stable to, dioxygen. The OMe analog 25 dissociates to form the radical 24, which reacts with dioxygen of TEMPO to give 26.

1,n-Radical ions. The photosensitized (electron transfer) formation of 1,5-radical cations

The photosensitized (electron transfer) reactions of 3-phenyl-2,3-dihydrobenzofuran (8a), 5-methyl-3-phenyl-2,3-dihydrobenzofuran (8b), cis and trans-2-methoxy-1-phenylindane (9, cis and trans), 3,3-diphenyltetrahydrofuran (10), and 2,2-diphenyl-1-methoxycyclopentane (11) have been studied using 1,4-dicyanobenzene as an electron-accepting photosensitizer and acetonitrile-methanol (3:1) as solvent.These reaction conditions cause carbon-carbon bond cleavage of analogous acyclic β,β-diphenylethyl ethers to give products derived from the diphenylmethyl radical and the α-oxycarbocation intermediates.The purpose of this study was to determine if this reaction could be applied to five-membered cyclic derivatives to give 1,5-radical cations.The primary products from 8a and 8b were the dehydrogenated, aromatized 3-phenylbenzofurans 14a and 14b.These products react further; continued irradiation gave the methanol adducts, cis and trans-2-methoxy-3-phenyl-2,3-dihydrobenzofuran (15a and 15b, cis and trans).The only observed reaction of the indanes (9, cis and trans) was cis-trans isomerization.Deuterium was incorporated at the bis-benzylic position of 8 and 9 when the irradiation was carried out in acetonitrile-methanol-O-d.These results are consistent with reversible deprotonation from the radical cations.There was no evidence for carbon-carbon bond cleavage with either 8 or 9.The relative rate, deprotonation faster than carbon-carbon bond cleavage, is explained in terms of the conformation of the bond that cleaves in relation to the singly occupied molecular orbital (SOMO) of the radical cation.Oxidation potential measurements support the conclusion that the SOMO of 8 and 9 is largely associated with the fused phenyl ring and is therefore orthogonal to the benzylic carbon-carbon bond.Irradiation of cis or trans-2-methoxy-3-phenyl-2,3-dihydrobenzofuran (15a, cis or trans), under these conditions, leads to cis-trans isomerisation.The mechanism in this case involves the reversible loss of methanol.There is evidence that the addition of methanol to 14 involves the sensitizer radical anion - 14 radical cation pair.In contrast with the fused bicyclic systems, the monocyclic tetrahydrofuran 10 and the methoxycyclopentane 11 both cleave under these conditions; the products are the expected acetals 22 and 29 formed from the intermediate 1,5-radical cations.In 10 and 11 the SOMO, which is largely associated with the diphenylmethyl moiety, can overlap with the adjacent carbon-carbon bond and cleavage occurs as in analogous acyclic systems.Both 10 and 11 are relatively stable to irradiation under conditions that are identical except with acetonitrile as solvent (without methanol).We found no evidence for cyclization of the intermediates (1,5-radical cation or 1,5-diradical) into the terminal phenyl ring.

Photochemical and Thermal Transformations of 2(3H)-Furanones and Bis(benzofuranones). A Laser Flash Photolysis study

Transformations of the 2(3H)-furanones 1-4 and bis(benzofuranones) 16-18 under steady-state photolysis and thermolysis are reported.Irradiation of 1 in benzene gives a mixture of the decarbonylated product 5 (62percent) and the cyclized phenanthrene derivative 10 (15percent).Similar results were obtained when the photolysis of 1 was carried out in methanol and acetone.Irradiation of 2 in benzene and methanol gave exclusively the decarbonylation product 6, whereas, in acetone, a mixture of the rearranged lactone 13 and and its cyclized product, 15, was obtained.Irradiation of both 3 and 4 gave the cyclized products 11 and 12, respectively.In contrast, the photolysis of the bis(benzofuranone) 16 in cyclohexane gave 3-phenylbenzo-2-(3H)-furanone (25), whereas the photolysis in methanol led to a mixture of methyl α-(2-hydroxyphenyl)phenylacetate (34) and 3-hydroxy-3-phenylbenzo-2(3H)-furanone (31).Similar results were obtained in the irradiation of 17 and 18.Neat thermolysis of furanones 1-3 at 350-450 deg C gave the decarbonylated products 5, 6, and 37 in 36-80 percent yields, whereas furanone 4 underwent facile isomerization to 5-benzyl-3,4,5-triphenyl-2(5H)-furanone (38), upon refluxing in diphenyl ether (ca. 255 deg C).Heating of bis(benzofuranones) 16-18 in refluxing cumene (ca. 150 deg C) gave the corresponding furanones 25-27 in 62-68 percent yields.Laser flash photolysis of furanones 1-4 at 248 and 337 nm leads to absorption spectral changes that can be explained in terms of singlet-mediated decarbonylation (φ = 0.3 for 2 in methanol, λex = 248 nm) and cyclization, i.e., dihydrophenanthrene formation (φ = 0.1-0.5 for 1, 3, and 4 in benzene and methanol, λex = 337 nm).The triplets of the furanones generated under energy-transfer sensitization by benzophenone in benzene are relatively long lived (r = 1.2-12 μs) and exhibit absorption maxima at 330-370 nm (εmax = (11-14) * 103 M-1 cm-1); these spectral and kinetic features appear to be characteristic of the styrene and cis-stilbene chromophores, constrained into planar configurations.Upon laser flash photolysis at 248 nm in methanol, bis(benzofuranones) 16-18 undergo facile fragmentation to the corresponding radicals 19-21, characterized by sharp and intense absorption maxima at ca. 330 nm, in addition to broad and weak absorption band systems at 500-600 nm; these radical species are the primary intermediates implicated in the formation of various final products in the course of steady-state photolysis of 16-18 under different conditions.