851789-43-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol is used as a key intermediate in the efficient synthesis of Tolterodine, a medication used for the treatment of overactive bladder and urinary incontinence. Its unique structure allows for the formation of specific chemical bonds and reactions that are crucial for the production of Tolterodine.
Used in Chemical Synthesis:
2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol is also used in the synthesis of various other chemicals and compounds, owing to its reactive functional groups and versatile chemical properties. Its ability to participate in a wide range of chemical reactions makes it a valuable building block in the development of new materials and products.

InChI:InChI=1/C16H18O2/c1-12-7-8-16(18)15(11-12)14(9-10-17)13-5-3-2-4-6-13/h2-8,11,14,17-18H,9-10H2,1H3

Upstream product

• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 349547-18-8 (S)-6-methyl-4-phenylchroman-2-one 
• 40546-94-9 6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 108-18-9 diisopropylamine 
• 106-44-5 p-cresol 
• 92-48-8 6-methylcoumarin 
• 98-80-6 phenylboronic acid 
• 827007-19-2 (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one 
• 828933-86-4 (4R)-6-methyl-4-phenylchroman-2-ol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4850-49-1 1-phenyl-1,3-propanediol 

Downstream Products

• 894773-88-7 3-(2-(ethanesulfonyloxy)-5-methylphenyl)-3-phenylpropyl-ethanesulfonate 
• 851789-45-2 3-(2-(p-toluenesulfonyloxy)-5-methylphenyl)-3-phenylpropyl-p-toluenesulfonate 
• 894773-87-6 3-(2-(benzenesulfonyloxy)-5-methylphenyl)-3-phenylpropyl-benzenesulfonate 
• 124937-52-6 tolterodine tartrate 
• 124936-74-9 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine 
• 854306-68-6 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol 

Relevant academic research and scientific papers

Computationally-Led Ligand Modification using Interplay between Theory and Experiments: Highly Active Chiral Rhodium Catalyst Controlled by Electronic Effects and CH–π Interactions

A chiral ligand for the rhodium-catalyzed asymmetric 1,4-addition of an arylboronic acid to a coumarin substrate that could markedly reduce catalyst loading was developed using interplay between theoretical and experimental approaches. Evaluation of the transition states for insertion and for hydrolysis of intermediate complexes (which were emphasized in response to the experimental results) using DFT calculations at the B97D/6-31G(d) level with the LANL2DZ basis set for rhodium revealed that: (i) the electron-poor nature of the ligands and (ii) CH–π interactions between the ligand and coumarin substrates played significant roles in both acceleration of insertion and inhibition of ArB(OH)2 decomposition (protodeboronation). The computationally-designed ligand, incorporating the above information, enabled a decrease in the catalyst loading to 0.025 mol% (S/C=4,000), which is less than one one-hundredth relative to past catalyst loadings of typically 3 mol%, with almost complete enantioselectivity. Furthermore, the gram-scale synthesis of the urological drug, (R)-tolterodine (l)-tartrate, was demonstrated without the need of intermediate purification. (Figure presented.).

Design, Synthesis, and Molecular Modeling of Asymmetric Tolterodine Derivatives as Anticancer Agents

An efficient and short enantioselective synthesis of (S)- and (R)-tolterodine acid isomers (7a–7i) was performed a 6-methyl-4-phenylchroman-2-one intermediate from inexpensive and commercially available starting materials. A series of tolterodine acid hyb

Synthesis and Antioxidant Properties of New Substituted 8-Methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide Derivatives

A new route for the synthesis of substituted 8-methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide derivatives has been developed by using cinnamic acid and p-cresol via condensation, reduction, and followed by phosphorylation steps. The ti

An efficient synthesis of racemic tolterodine

The efficient and cost effective of the synthesis of (±)-tolterodine (1), a precursor of (+)-(R)-tolterodine was efficiently performed from 6-methyl-4-chroman-2-one (2) via 4 steps in high yield. This process is suitable for large-scale commercial production by avoiding hazardous reagents and high pressure of hydrogen gas.

Co-catalyzed mild and chemoselective reduction of phenyl esters with NaBH4: a practical synthesis of (R)-tolterodine

CoCl2 catalyzes effectively the chemoselective reduction of phenyl carboxylic esters to the corresponding saturated alcohols in high yields using NaBH4 at ambient conditions. By employing this methodology, the synthesis of (R)-tolterodine, a muscarinic receptor antagonist, has been achieved in high yield and optical purity.

Enantioselective synthesis of (S)- and (R)-tolterodine by asymmetric hydrogenation of a coumarin derivative obtained by a Heck reaction

(Chemical Equation Presented) An efficient and short enantioselective synthesis of (S)- and (R)-tolterodine was performed by asymmetric hydrogenation of a coumarin intermediate, easily obtained by a Heck reaction from inexpensive and commercially available starting materials.

Reduction of ethyl benzoylacetate and selective protection of 2-(3-hydroxy-1-pheny|propyl)4-methylphenol: A new and facile synthesis of tolterodine

A new and facile synthesis of tolterodine using ethyl benzoylacetate as the starting material was developed. Reduction using sodium borohydride in methanol followed by Friedel-Crafts alkylation utilizing FeCl3 ·6H2O as catalyst lead to the known 2-(3-hydroxyl- phenylpropyl)-4-methylphenol intermediate. Consecutive protection of phenolic OH withp-toluenesulfonyl chloride via two-phase reaction and conversion of aliphatic OH using p-nitrobenzenesulfonyl chloride facilitates direct substitution of duesopropylamine. After simultaneous deprotection of the tosyl group, optically pure (R)-tolterodine·L-tartrate was obtained by resolution using L-tartaric acid with 99.99% purity.

PROCESS FOR PREPARATION OF 3-(2-HYDROXY-5-METHYLPHENYL)-N,N-DIISOPROPYL-3-PHENYLPROPYLAMINE

A new process for preparation of 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropylamine from 3,4-dihydro-6-methyl-4-phenyl-2-benzopyran-2-one is characterized by intermediates such as 3-(2-hydroxy-5-methyl phenyl)-3- phenylpropanol and its sulph

Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine

A process is described for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine comprising substitution of the sulfonyloxy group of the compound of the formula in which the substituents R and R″ have the meanings stated in the description, in a solvent comprising an ionic liquid, to yield the tertiary amine of the formula and the subsequent deprotection thereof.

ENANTIOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY ENRICHED COMPOUNDS

Method of preparing an enantiomerically enriched compound of formula (II) comprising enantioselective hydrogenation of a compound of general formula (I): where W, X and Z have the meanings indicated in the description, to give a compound of general formula (II): where W, Y, T and C* have the meanings indicated in the description, in the presence of a catalyst or its suitable precursor based on Rh, Ru or Ir, having an oxidation state of 0, +1 or +2, and containing at least one enantiomerically enriched chiral ligand.