59771-24-3

Usage

Uses

4'-Isobutylpropiophenone is a reagent used in the continuous-flow synthesis of Ibuprofen.

Synthesis Reference(s)

Synthetic Communications, 21, p. 1473, 1991 DOI: 10.1080/00397919108016420

InChI:InChI=1/C13H18O/c1-4-13(14)12-7-5-11(6-8-12)9-10(2)3/h5-8,10H,4,9H2,1-3H3

Upstream product

• 538-93-2 1-phenyl-2-methylpropane 
• 79-03-8 propionyl chloride 
• 80336-66-9 2-chloro-1-(4-isobutyl-phenyl)1-propanone 
• 104-51-8 1-butylbenzene 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 66202-89-9 p-isobutylpropiophenone dimethyl ketal 
• 80336-64-7 2-bromo-1-(4'-isobutyl-phenyl)-propan-1-one 
• 802294-64-0 propionic acid 

Downstream Products

• 80336-64-7 2-bromo-1-(4'-isobutyl-phenyl)-propan-1-one 
• 80336-63-6 2-(1-bromoethyl)-2-[4-(2-methylpropyl)-phenyl]-1,3-dioxolane 
• 59771-03-8 1-bromo-1-(4-isobutylphenyl)propane 
• 139154-75-9 ethyl 4-[3-[4-[1-(4-isobutylphenyl)propoxy]benzoyl]-indol-1-yl]butyrate 
• 146923-37-7 ethyl (+/-)-4-[1-[4-[1-(4-isobutylphenyl)propyloxy]benzoyl]indolizin-3-yl]butyrate 
• 148366-90-9 4-(3-{4-[(R)-1-(4-Isobutyl-phenyl)-propoxy]-benzoyl}-indol-1-yl)-butyric acid ethyl ester 
• 148366-89-6 4-(3-{4-[(S)-1-(4-Isobutyl-phenyl)-propoxy]-benzoyl}-indol-1-yl)-butyric acid ethyl ester 
• 129159-22-4 2-hydroxy-1-(4-isobutylphenyl)-1-propanone 
• 151647-67-5 (R)-2-hydroxy-1-(4-isobutylphenyl)-1-propanone 
• 169295-48-1 2-acetoxy-1-(4-isobutylphenyl)-1-propanone 
• 100743-63-3 (S)-1,1-dimethoxy-1-(4-isbutylphenyl)-2-propanol 
• 169295-51-6 (R)-1-(4-isbutylphenyl)-2-methylsulfonyloxy-1-propanone 
• 91306-41-1 2-(4-Isobutyl-phenyl)-2-(1-phenylselanyl-ethyl)-[1,3]dioxolane 
• 91306-46-6 2-(4-Isobutyl-phenyl)-2-(1-phenyltellanyl-ethyl)-[1,3]dioxolane 

Relevant academic research and scientific papers

A 4 - isobutyl phenyl ketone compounds (by machine translation)

The invention discloses a 4 - isobutyl phenyl ketone compounds, the compound structure is as follows: said compound 4 - isobutyl-benzene as the starting material, substituted sulfonic acid and substituted sulfonate as the catalyst, the reaction with the acyl chloride, the following reaction: the application of this method to synthesize 4 - isobutyl phenyl ketone compound, simple and convenient operation, mild reaction conditions, environment-friendly, and has excellent industrial prospect. (by machine translation)

Synthesis method of silver aldehyde spice

The invention discloses a synthesis method of a silver aldehyde spice and relates to the technical field of fine chemical engineering. Isobutyl benzene and propionyl chloride are used as starting raw materials, silver aldehyde is synthesized through acylation reaction and hydrodechlorination, the raw materials in use are easy to obtain, and the product yield is high. Ethyl alcohol serves as an organic solvent for hydrogenation reaction, the shortcomings of incomplete reaction or excessive hydrogenation and inactivation after mechanical application of a catalyst in the hydrogenation process are overcome, the content of meta-position silver aldehyde and ortho-position silver aldehyde during side reaction is controlled to be 0.5% or below, the content of 2-methyl-3(4-(2-methyl propyl) phenyl) propyl alcohol in a silver aldehyde finished product is controlled to be 0.5% or below, the unimodal content of the silver aldehyde product can be 98.5% or above, and the silver aldehyde spice has a pure and soft aroma and meets the flavoring requirements of essences and spices.

Synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde

The invention discloses a synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde and relates to the technical field of fine chemical engineering. The synthesis method includes: using isobutylbenzene and propionyl chloride as raw materials, and generating p-isobutyl propiophenone through acylation reaction; enabling p-isobutyl propiophenone to be in acylation reaction with phosphorus oxychloride to obtain a silver aldehyde precursor- p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde. The synthesis method is easy-to-get in raw materials, high in yield and convenient for industrial large-scale production; content of byproducts-ortho- and meta-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde is controlled below 0.2%, and impurity content in a final silver aldehyde product prepared after hydrodechlorination is controlled effectively, so that flavoring requirements of essence and flavor are met.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

The digital code driven autonomous synthesis of ibuprofen automated in a 3D-printer-based robot

An automated synthesis robot was constructed by modifying an open source 3D printing platform. The resulting automated system was used to 3D print reaction vessels (reactionware) of differing internal volumes using polypropylene feedstock via a fused deposition modeling 3D printing approach and subsequently make use of these fabricated vessels to synthesize the nonsteroidal antiinflammatory drug ibuprofen via a consecutive one-pot three-step approach. The synthesis of ibuprofen could be achieved on different scales simply by adjusting the parameters in the robot control software. The software for controlling the synthesis robot was written in the python programming language and hard-coded for the synthesis of ibuprofen by the method described, opening possibilities for the sharing of validated synthetic 'programs' which can run on similar low cost, user-constructed robotic platforms towards an 'open-source' regime in the area of chemical synthesis.

A three-minute synthesis and purification of ibuprofen: Pushing the limits of continuous-flow processing

In a total residence time of three minutes, ibuprofen was assembled from its elementary building blocks with an average yield of above 90% for each step. A scale-up of this five-stage process (3 bond-forming steps, one work-up, and one in-line liquid-liquid separation) provided ibuprofen at a rate of 8.09 gh-1 (equivalent to 70.8 kg y-1) using a system with an overall footprint of half the size of a standard laboratory fume hood. Aside from the high throughput, several other aspects of this synthesis expand the capabilities of continuous-flow processing, including a Friedel-Crafts acylation run under neat conditions and promoted by AlCl3, an exothermic in-line quench of high concentrations of precipitation-prone AlCl3, liquid-liquid separations run at or above 200 psi to provide solvent-free product, and the use of highly aggressive oxidants, such as iodine monochloride. The use of simple, inexpensive, and readily available reagents thus affords a practical synthesis of this important generic pharmaceutical.

DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones

A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).

The continuous-flow synthesis of ibuprofen

Let relief flow forth I A three-step, continuous-flow synthesis of ibuprofen was accomplished using a simplified microreactor. By designing a synthesis in which excess reagents and byproducts are compatible with downstream reactions, no intermediate purification or isolation steps are required.

5-Aryl-imidazolin-2-ones as a scaffold for potent antioxidant and memory-improving activity

A series of 5-phenyl-substituted-N-alkyl-imidazolin-2-ones with potent radical-scavenging activity and lipid peroxidation inhibitory activity was synthesized. Many of the compounds showed memory-improving effect in animal models independent of the inhibitory activity on lipid peroxidation.

4-(Benzoylindolizinyl)butyric acids; novel nonsteroidal inhibitors of steroid 5α-reductase. III

A novel series of indolizinebutyric acids with various benzoyl substituents was synthesized to develop nonsteroidal inhibitors of steroid 5α-reductase, and the structure-activity relationships in this series were studied. We previously reported the structure-activity relationships in a series of indolebutyric acids as well as the discovery of the novel nonsteroidal 5α-reductase inhibitor, FK143. We have now made other modifications to this compound to improve in vivo inhibitory activity. By altering the heterocyclic nucleus and changing the benzoyl substituent we have succeeded in identifying the strongly active compound, FK687, (S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yllbutyric acid, which displays strong in vitro inhibitory activity against the human enzyme and in vivo inhibitory activity against the castrated young rat model. This compound should be a useful agent for the treatment of benign prostatic hyperplasia.