35144-34-4

Upstream product

• 917-64-6 methyl magnesium iodide 
• 252058-33-6 2-(4-methoxyphenyl)propanal 
• 75-16-1 methylmagnesium bromide 
• 98815-48-6 1-bromo-2-(4-methoxyphenyl)propan-2-ol 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 
• 38454-63-6 Z-2-(4-methoxyphenyl)-2-butene 
• 30068-21-4 2-(4-methoxyphenyl)-1-methyl-2-propanol 
• 42432-42-8 1,2-epoxy-2-(4'-methoxyphenyl)propane 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 7074-12-6 3-(4-methoxyphenyl)butan-2-one 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 

Downstream Products

• 111325-89-4 (+/-)-phthalic acid mono-[(rel-1R,2R)-2-(4-methoxy-phenyl)-1-methyl-propyl ester] 
• 111325-89-4 phthalic acid mono-[(rel-1R,2R)-2-(4-methoxy-phenyl)-1-methyl-propyl ester] 
• 111325-89-4 (+/-)-phthalic acid mono-[(rel-1R,2S)-2-(4-methoxy-phenyl)-1-methyl-propyl ester] 
• 111325-89-4 phthalic acid mono-[(rel-1R,2S)-2-(4-methoxy-phenyl)-1-methyl-propyl ester] 
• 132467-09-5 (+/-)-threo-2-(4-methoxy-phenyl)-3-(4-nitro-benzoyloxy)-butane 
• 132467-09-5 (+/-)-erythro-2-(4-methoxy-phenyl)-3-(4-nitro-benzoyloxy)-butane 

Relevant academic research and scientific papers

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

Reactions of 4-Substituted-2'-Halogenoacetophenones with Grignard Reagents

The initial reaction of 4-substituted 2'-halogenoacetophenones with an excess of methyl Grignard reagent is shown to be an attack at the 1'-carbonyl to form a halohydrin salt.The various reactions which then follow are substituent dependent.In the 4-hydroxy case the only product is 1-(4-hydroxyphenyl)-2-methylpropan-2-ol (13) which arises via a -aryl shift with simultaneous elimination of magnesium halide.When the substituent is 4-methoxy, a second pathway becomes important involving epoxide formation and a subsequent -hydride migration to the benzylic position, or attack of the Grignard reagent at the benzylic carbon of the epoxide.When the substituent is 4-bromo, the reaction proceeds exclusively via the epoxide and, following a -hydride shift, leads to the isomeric butanols (33) and (34).The reasons underlying such diversity of reactivity are discussed.