66306-86-3

Upstream product

• 118-55-8 phenyl Salicylate 
• 100-61-8 N-methylaniline 
• 69-72-7 salicylic acid 
• 224432-01-3 N-methyl-N-phenyl-2-acetoxybenzamide 
• 50-78-2 aspirin 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 444-30-4 2-(trifluoromethyl)phenol 
• 1441-87-8 salicyloyl chloride 
• 1934-92-5 N-methyl-N-phenyl-benzamide 
• 394-47-8 2-fluorobenzonitrile 
• 40501-36-8 2-phenoxybenzoyl chloride 

Downstream Products

• 90-02-8 salicylaldehyde 
• 1400883-69-3 C₂₁H₁₉NO₄S 
• 333442-01-6 C₁₆H₁₇NO₂ 

Relevant academic research and scientific papers

Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution

Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.

Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation

A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.

A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp2)-H hydroxylation strategy

A diversity-oriented synthesis of bioactive benzanilides via C(sp2)-H hydroxylation has been studied. Different regioselectivity was observed with Ru(ii) and Pd(ii) catalysts. The reaction demonstrates excellent regioselectivity, good tolerance

Intramolecular metal-free oxidative aryl-aryl coupling: An unusual hypervalent-iodine-mediated rearrangement of 2-substituted n-phenylbenzamides

Hypervalent-iodine-mediated oxidative coupling of the two aryl groups in either 2-acylamino-N-phenyl-benzamides or 2-hydroxy-N-phenylbenzamides, with concomitant insertion of the ortho-substituted N or O atom into the tether, has been described for the first time. This unusual metal-free rearrangement reaction involves an oxidative C(sp2)?C(sp2) aryl-aryl bond formation, cleavage of a C(sp2)?C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product.

Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups

Figure presented In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%).

Novel Enzymatic De-esterification Studies on Substituted Polyacetoxybenzamides

The regioselective capabilities of porcine pancreatic lipase in tetrahydrofuran and Candida rugosa lipase in diisopropyl ether have been investigated for selective deacetylation of peracetates of primary, secondary and tertiary amides of 2-hydroxy-, 2,4-dihydroxy-, 2,5-dihydroxy-, 3,5-dihydroxy- and 3,4,5-trihydroxybenzoic acids. The lipases exhibit random selectivity for the deacetylation of ortho-, meta- and para-acetoxy functions of di/triacetoxybenzamides leading to the formation of the corresponding partially and/or completely deacetylated benzamides. The amide group of all substrates under investigation remains inert to enzymatic hydrolysis. The results of deesterification are in good agreement with our earlier proposed mechanism of action of porcine pancreatic lipase on diaryl or aryl alkyl ketones in organic solvents.

Pyrolysis of O-Allyl Salicylic Amides and Esters, and Related Compounds: Foemation of Isoindolones and Phthalides

Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl esters gives isoindolones and phthalides, respectively, in low (20-40percent) yield.The mechanism involves generation of the phenoxyl radical, regiospecific hydrogen-atom transfer from the alkylamide (or alkyl ester) group and cyclization.A similar sequence was observed with thiophenoxyl radicals.