4927-54-2

Usage

Uses

Used in Pharmaceutical Industry:
Ethanone, 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)is used as a building block for the synthesis of pharmaceuticals due to its potential biological activity. The presence of methoxyphenyl groups in its structure allows for the development of new drugs with specific therapeutic properties.
Used in Flavor and Fragrance Industry:
Ethanone, 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)is also used in the production of fragrances and flavors, where its unique chemical structure contributes to the creation of distinct scents and tastes.

Upstream product

• 104-47-2 p-methoxybenzylnitrile 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 104-01-8 4-Methoxyphenylacetic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 4693-91-8 4-methoxyphenyl-acetic chloride 

Downstream Products

• 84675-73-0 1-(3,4-Dimethoxy-phenyl)-2-(4-methoxy-phenyl)-butan-1-one 
• 86633-28-5 3,4,4'-trimethoxydeoxybenzoin ethylene acetal 
• 102520-84-3 Acetic acid 2-acetoxy-5-[(Z)-2-(4-acetoxy-phenyl)-1-phenyl-but-1-enyl]-phenyl ester 
• 102520-85-4 Acetic acid 2-acetoxy-5-[(E)-2-(4-acetoxy-phenyl)-1-phenyl-but-1-enyl]-phenyl ester 
• 86633-36-5 2-(ethoxycarbonyl)-3,4,4'-trimethoxydeoxybenzoin 
• 101582-88-1 3,4,4'-trimethoxy-bibenzyl-α-ylamine 
• 225666-33-1 6-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)-2H-pyridazin-3-one 

Relevant academic research and scientific papers

Regioselection in the synthesis of 4-benzyltetral-1-ones and the new 4-arylbenzosuber-1-ones

The intramolecular Friedel-Crafts acylation of 4,5-diarylpentanoic acids has the possibility to cyclise to either a 6-membered ring to give 4-benzyltetral-1-one or a 7-membered ring to give 4-arylbenzosuber-1-one. Of these, only the former compound class has previously been reported. The impact of the substituents positioning on the outcome of the cyclisation has been investigated. The complete formation of either the tetralone or the benzosuberone regioisomer was possible under the same reaction conditions, dependent upon the ring activation and/or deactivation of the chosen substituents. Selected bromo or methoxy substituents could be used as auxiliaries, included in precursors to afford the desired regioisomer and then subsequently removed.

Synthesis of substituted phenanthrofurans

A three-step protocol toward phenanthrofurans 1 starting with deoxybenzoins 3 is developed with moderate to good yield. A facile process is carried out for the (1) α-propargylation of 3 with NaH and propargyl bromide 2 in refluxing THF, (2) Bi(OTf)3-mediated cycloisomerization of γ-ynones 4 with 4 ? molecular sieves in MeNO2 at rt, and (3) photolytic Scholl annulation of 2,3-diarylfurans 5 with I2 in EtOAc at rt. The key structures of 1 are confirmed by X-ray crystallographic analysis.

Influence of Alkoxyalkyl Substituents in the Regioselective Lithiation of the Benzene Ring

The concomitant presence of an alkoxyalkyl group (α-alkoxyalkyl, α- or β-dialkoxyalkyl) and of an alkoxy group in the relative positions 1 and 3 in a benzene ring generally permits an easy lithiation of position 2 by proton-metal exchange with n-butyllithium; the only aromatic compound tested, bearing a β-alkoxyalkyl group, gave, however, extensive decomposition in the metalation step.Reaction of the metalated species with an electrophile (such as carbon dioxide or ethyl chloroformate) leads to the corresponding substituted products in good to excellent yields.The following transformations are described: 3,4-dimethoxybenzyl α-ethoxyethyl ether (1) into 6,7-dimethoxyphthalide (15); 3,4-(methylenedioxy)benzyl α-ethoxyethyl ether (2) into 6,7-(methylenedioxy)phthalide (16); 3,4-dimethoxybenzyl methyl ether (3) into ethyl 2-(methoxymethyl)-5,6-dimethoxybenzoate (18) and into ethyl 2-(chloromethyl)-5,6-dimethoxybenzoate (20); 3,4-(methylenedioxy)benzyl methyl ether (4) into ethyl 2-(methoxymethyl)-5,6-(methylenedioxy)benzoate (19) and into ethyl 2-(chloromethyl)-5,6-(methylenedioxy)benzoate (21); 3,4-dimethoxybenzaldehyde dimethyl acetal (5) into 5,6-dimethoxyphthalaldehydic acid (22); 3,4-(methylenedioxy)benzaldehyde dimethyl acetal (6) into 5,6-(methylenedioxy)phthalaldehydic acid (23); (3,4-dimethoxyphenyl)acetaldehyde dimethyl acetal (7) into ethyl 2-(2,2-dimethoxyethyl)-5,6-dimethoxybenzoate (25); 3,4,4'-trimethoxydeoxybenzoin ethylene acetal (10) into 2-(ethoxycarbonyl)-3,4,4'-trimethoxydeoxybenzoin (26); 4,3',4'-trimethoxydeoxybenzoin ethylene acetal (11) into 2'-(ethoxycarbonyl)-4,3',4'-trimethoxydeoxybenzoin (27); 3,4,3',4'-tetramethoxydeoxybenzoin ethylene acetal (12) into a mixture of 3-(3,4-dimethoxybenzylidene)-6,7-dimethoxyphthalide (28) and 3-(3,4-dimethoxyphenyl)-7,8-dimethoxyisocoumarin (29).The dioxole ring of methylenedioxy-substituted benzenes is sometimes unstable under these metalation conditions, and partial decomposition usually causes the yields to be lower than those in the case of the corresponding methoxy-substituted benzenes.Many of the products listed above, which have been already prepared by other methods, are more conveniently obtained by the present approach.