6-Methyl-4-phenyl-2-chromanol

Base Information

• Chemical Name: 6-Methyl-4-phenyl-2-chromanol
• CAS No.: 209747-04-6
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• UNII: K8U68SF3V5
• DSSTox Substance ID: DTXSID50459483
• Nikkaji Number: J2.102.118K
• Mol file: 209747-04-6.mol

Synonyms:209747-04-6;6-Methyl-4-phenyl-2-chromanol;TOLTERODINE IMPURITY 13;2H-1-Benzopyran-2-ol, 3,4-dihydro-6-methyl-4-phenyl-;6-methyl-4-phenyl-3,4-dihydro-2H-chromen-2-ol;rac-6-Methyl-4-phenyl-2-chromanol;3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-ol;K8U68SF3V5;6-Methyl-4-phenylchroman-2-ol;TOLTERODINEIMPURITY13;UNII-K8U68SF3V5;SCHEMBL815552;2H-1-Benzopyran-2-ol,3,4-dihydro-6-methyl-4-penpyl-;DTXSID50459483;JGRSOLBFAHJDTL-UHFFFAOYSA-N;AKOS030254919;J-013743;3,4-dihydro-6-methyl-4-phenyl-2h-1-benzopyran-2-ol;4-Phenyl-6-methyl-3,4-dihydro-2H-1-benzopyran-2-ol;6-methyl-4-phenyl-3,4-dihydro-2h-1-benzopyran-2-ol

Chemical Property of 6-Methyl-4-phenyl-2-chromanol

Chemical Property:

• Melting Point: 80-81 °C
• Boiling Point: 377.2±42.0 °C(Predicted)
• PKA: 12.71±0.40(Predicted)
• PSA: 29.46000
• Density: 1.173±0.06 g/cm3(Predicted)
• LogP: 3.22780
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 240.115029749
• Heavy Atom Count: 18
• Complexity: 272

Purity/Quality:

97% ^*data from raw suppliers

rac-6-Methyl-4-phenyl-2-chromanol(TolterodineImpurity)(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)OC(CC2C3=CC=CC=C3)O
• Uses: rac-6-Methyl-4-phenyl-2-chromanol is an impurity of Tolterodine (T535800), an antimuscarinic agent used to treat patients with overactive bladder.

Technology Process of 6-Methyl-4-phenyl-2-chromanol

There total 9 articles about 6-Methyl-4-phenyl-2-chromanol 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: 66.0%

6-methyl-4-phenyl-3,4-dihydrocoumarin (40546-94-9) → 2-hydroxy-6-methyl-4-phenyldihydrobenzopyran (209747-04-6)

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; at -78 ℃; for 2.5h;

DOI:10.1016/j.tetasy.2017.04.001

Reference yield: 48.0%

(E)-3-phenylpropenal (14371-10-9) + p-cresol (106-44-5) → 2-hydroxy-6-methyl-4-phenyldihydrobenzopyran (209747-04-6)

Guidance literature:

(E)-3-phenylpropenal; p-cresol; morpholine; at 100 ℃; for 6h;

With hydrogenchloride; In water; at 75 - 80 ℃; for 12.75h; Product distribution / selectivity;

Reference yield:

6-methyl-4-phenyl-3,4-dihydrocoumarin (40546-94-9) + diisopropylamine (108-18-9) → 3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1 (851789-43-0) + (R)-(+)-tolterodine (124937-51-5,124937-53-7) + 2-hydroxy-6-methyl-4-phenyldihydrobenzopyran (209747-04-6)

Guidance literature:

6-methyl-4-phenyl-3,4-dihydrocoumarin; With diisobutylaluminium hydride; In toluene; at -25 ℃; for 5h;

With citric acid; In water; ethyl acetate; toluene; at 20 ℃;

diisopropylamine; With hydrogen; 5%-palladium/activated carbon; In methanol; at 48 ℃; for 12h; under 3800.26 Torr;

upstream raw materials:

1,4-bis-(6-methyl-4-phenyl-chroman-2-yl)-piperazine

(E)-3-phenylpropenal

p-cresol

6-methyl-4-phenyl-3,4-dihydrocoumarin

Downstream raw materials:

N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine

4-methyl-2-(1-phenyl-3-pyrrolidine-1-ylpropyl)phenol