Ibuprofen alcohol, (+)-

Base Information

• Chemical Name: Ibuprofen alcohol, (+)-
• CAS No.: 93673-13-3
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• UNII: 14TRB9JHZ8
• Nikkaji Number: J1.664.893K
• Wikidata: Q27251648
• Mol file: 93673-13-3.mol

Synonyms:Ibuprofen alcohol, (+)-;14TRB9JHZ8;UNII-14TRB9JHZ8;93673-13-3;Benzeneethanol, beta-methyl-4-(2-methylpropyl)-, (R)-;Benzeneethanol, beta-methyl-4-(2-methylpropyl)-, (betaR)-;(+)-ibuprofen alcohol;SCHEMBL9520092;(R)-2-(4-Isobutylphenyl)-1-propanol;EN300-6506557;(2R)-2-[4-(2-methylpropyl)phenyl]propan-1-ol;Q27251648;BENZENEETHANOL, .BETA.-METHYL-4-(2-METHYLPROPYL)-, (R)-;BENZENEETHANOL, .BETA.-METHYL-4-(2-METHYLPROPYL)-, (.BETA.R)-

Chemical Property of Ibuprofen alcohol, (+)-

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 145

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)CO
• Isomeric SMILES: C[C@@H](CO)C1=CC=C(C=C1)CC(C)C

Technology Process of Ibuprofen alcohol, (+)-

There total 17 articles about Ibuprofen alcohol, (+)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

2-(4-isobutylphenyl)propionaldehyde (51407-46-6) + homophthalic anhydride (703-59-3) + diazomethyl-trimethyl-silane (18107-18-1) → methyl (3R,4R)-3-((S)-1-(4-isobutylphenyl)ethyl)-1-oxoisochromane-4-carboxylate + (2R)-2-<4-(2-methylpropyl)phenyl>propan-1-ol (93673-13-3)

Guidance literature:

2-(4-isobutylphenyl)propionaldehyde; homophthalic anhydride; With 3-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)-4-(((S)-2-oxo-1-phenyl-2-(pyrrolidin-1-yl)ethyl)amino)cyclobut-3-ene-1,2-dione; In tetrahydrofuran; tert-butyl methyl ether; at -78 ℃; for 108h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; tert-butyl methyl ether; at -78 ℃; for 0.166667h; Inert atmosphere;

diazomethyl-trimethyl-silane; In tetrahydrofuran; methanol; diethyl ether; tert-butyl methyl ether; at 0 ℃; for 0.166667h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201902422

Reference yield:

C21H26O2 → (R)-1-phenylethanol (1517-69-7) + (2R)-2-<4-(2-methylpropyl)phenyl>propan-1-ol (93673-13-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 4h; Title compound not separated from byproducts.;

DOI:10.1016/j.tetasy.2007.09.015

Reference yield:

(R)-ibuprofen methyl ester (81576-57-0) → (2R)-2-<4-(2-methylpropyl)phenyl>propan-1-ol (93673-13-3)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In ethanol; at -20 ℃;

DOI:10.1002/jhet.5570260313

upstream raw materials:

(R)-ibuprofen methyl ester

vinyl acetate

2-(4-isobutylphenyl)propan-1-ol

(R)-2-(p-isobutylphenyl)-1,2-propanediol

Downstream raw materials:

(2R)-2-<4-(2-Methylpropyl)phenyl>propanal

(4R)-2-<(1R)-1-(4-(2-Methylpropyl)phenyl)ethyl>thiazolidine-4-carboxylic Acid

Refernces

• 1、 Farid, Umar,Aiello, Maria Luisa,Connon, Stephen J.. "Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides". supporting information. p. 10074 - 10079. Retrieved 2019/07/18.
• 2、 Coulbeck, Elliot,Eames, Jason. "Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts". . p. 2313 - 2325. Retrieved 2008/03/18.