51686-49-8

Upstream product

• 67-56-1 methanol 
• 107-93-7 (E)-but-2-enoic acid 
• 2859-78-1 4-Bromoveratrole 
• 95152-22-0 (2E)-N-(4-methoxyphenyl)-2-butenamide 
• 201230-82-2 carbon monoxide 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 91-16-7 1,2-dimethoxybenzene 
• 14563-40-7 methyl 4-(3,4-dimethoxyphenyl)-4-oxobutanoate 
• 5333-34-6 3-(3,4-dimethoxybenzoyl)propionic acid 

Downstream Products

• 436155-48-5 methyl 2-[4-(3,4-dimethoxyphenyl)butanoyl]hydrazinecarboxylate 
• 436155-34-9 4-(3,4-dimethoxyphenyl)butanoylhydrazine 

Relevant academic research and scientific papers

Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate

Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+═C═O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 °C. The present reaction provides a route to eight- A nd nine-membered benzolactams.

Pd-Catalyzed Regioselective Alkoxycarbonylation of 1-Alkenes Using a Lewis Acid [SnCl2 or Ti(OiPr)4] and a Phosphine

The phosphine ligand mediated palladium catalyzed alkoxycarbonylation of alkenes was investigated with the objective of attaining good linear selectivity for the ester. The effect of various parameters such as solvents, additives, palladium precursors, CO pressures, and alkenes of various structural complexities were examined. The results revealed the importance of using a Lewis acid such as SnCl2 or Ti(OiPr)4 in combination with a monodentate ligand such CYTOP 292 or P(p-anisyl)3 to enhance the regioselectivity for the linear isomers in the range of 70-96%.

Reaction of 2-Butenoic Acid Dianion and Its N-(4-Methoxyphenyl)amide with Methoxy-Substituted Arynes

N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide (9) (85-90percent) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15percent).Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amountsof 4-aryl-2-butenoic acids 15'.The exclusive low temperature (-30 to -40 deg C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures.The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.