82807-53-2

Upstream product

• 110-91-8 morpholine 
• 7204-35-5 2-(dimethylamino-methyl)-4-methyl-phenol 
• 106-44-5 p-cresol 
• 75-09-2 dichloromethane 
• 5720-05-8 4-methylphenylboronic acid 
• 50-00-0 formaldehyd 
• 569646-48-6 [2-(tert-butyl-diphenyl-silanyloxy)-5-methyl-benzyl]-dimethyl-amine 
• 569646-46-4 4-Methyl-2-{[morpholin-4-ylmethyl-((R)-1-phenyl-ethyl)-amino]-methyl}-phenol 
• 237431-64-0 6-methyl-3-[(1R)-1-phenylethyl]3,4-dihydro-2H-1,3-benz[e]oxazine 
• 569646-47-5 4-Methyl-2-[((R)-1-phenyl-ethylamino)-methyl]-phenol 
• 67853-12-7 (2-hydroxy-5-methyl-benzyl)-trimethyl-ammonium; iodide 

Relevant academic research and scientific papers

Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols

A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical coupling mechanism involving a six-membered transition state is proposed to rationalize the high levels of ortho-selectivity in the reaction. This protocol provides straightforward access to ortho-aminomethyl-substituted phenols, unnatural amino acids and other bioactive small molecules.

The modified-Mannich reaction: Conversion of arylboronic acids and subsequent coupling with paraformaldehyde and amines toward the one-pot synthesis of Mannich bases and benzoxazines

A modified Mannich reaction has been developed for the synthesis of Mannich bases and benzoxazines via the oxidative hydroxylation of arylboronic acids and subsequent coupling with paraformaldehyde and amines in one pot. This modified Mannich reaction is easily carried out to afford the target products in good to excellent yields and tolerates a variety of functional groups.

Synthesis of N-[2-hydroxy-4(5)-methyl- and -5-(methylcyclohexyl)benzyl] morpholines as antioxidants for transformer oils

Aminomethylation of m- and p-cresols and of p-(1-methylcyclohexyl)phenol with formaldehyde and morpholine was studied. The products obtained were tested as antioxidant additives to T-1500 transformer oil.

Reaction on a solid surface - A simple, economical, and efficient Mannich reaction of azacrown ethers over graphite

Graphite brings about a rapid Mannich reaction with a range of activated and unactivated phenolic compounds such as p-cresol and p-nitrophenol. The reactions are carried out with azacrown ether and paraformaldehyde in solvent-free conditions at 100 °C for 20-30 min. The graphite powder can be reused up to three times after simple washing with acetone.

Regioselective mannich reaction of phenols under high pressure using dichloromethane as C1 unit

Regioselectivity in Mannich reaction of 4-, 3-, and 2-substituted phenols with typical heterocyclic amines are investigated under reaction conditions developed by us. Phenol and 4-alkyl, and 4-chlorophenols in the title reaction predominantly gave the corresponding 2-(aminomethyl)phenols, while 4-methoxyphenol afforded, in addition to the mono(aminomethyl)phenols, a considerable amount of the bis adducts. Peculiarly enough, 3-methylphenol with amines afforded 3-methyl-4-(aminomethyl)phenols whereas 2-methylphenol produced 2-methyl-6-(aminomethyl)phenols.

Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines and the synthesis of axially chiral resorcinarenes

Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions.

Synthesis of phenols and naphthol with n-morpholinomethyl pendants and their dimethylgallium complexes: Crystal structure of dimethylgallium-[4-nitro-2-(n-morpholinomethyl)-1-phenoxide]

The one-pot Mannich reaction was used to synthesize 2-(n-morpholinomethyl)-1-phenol (1a), 4-methyl-2-(n-morpholinomethyl)-1-phenol (1b), 4-chloro-2-(n-morpholinomethyl)-1-phenol (1c), 4-nitro-2-(n-morpholinomethyl)-1-phenol (1d), and 1-(n-morpholinomethyl)-naphthol (1e). The dimethylgallium complexes of these compounds have been prepared, and compound 2d has been determined by X-ray crystallography. The complex 2d crystallized with one unit having two identical molecules which have intermolecular contacts between the two phenyls caused by face to face π-π stacking. The Ga-O bond distances are noticeably shorter than in the other dimethylgallium phenoxides reported.