3-(2-Methoxy-5-methylphenyl)-3-phenyl propanol Chemical Properties

Boiling point:

413.8±33.0 °C(Predicted)

Density 

1.066±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.94±0.10(Predicted)

CAS DataBase Reference

124937-73-1(CAS DataBase Reference)

3-(2-Methoxy-5-methylphenyl)-3-phenyl propanol Usage And Synthesis

Uses

2-Methoxy-5-methyl-γ-phenylbenzenepropanol is a related compound to Tolterodine (T535795), a muscarinic receptor antagonist. Used in the treatment of urinary incontinence.

Synthesis

General procedure for the synthesis of 3-(2-methoxy-5-methylphenyl)-3-phenylpropanol from 3-(2-methoxy-5-methylphenyl)-3-phenyl-1-propanol: Over a period of 2 hours, 0.5 kg of 3-(2-methoxy-5-methylphenyl)-3-phenylpropanoic acid dissolved in 2.0 L of tetrahydrofuran was added slowly and dropwise to 0.105 kg of sodium borohydride containing a 0.5 L of tetrahydrofuran suspension. After the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Subsequently, 0.177 kg of methanesulfonic acid was slowly added over 1 hour. After addition, stirring was continued at room temperature for 1 hour. The reaction mixture was heated to 65-70°C and stirring was maintained for 8-10 hours. Upon completion of the reaction, it was cooled to 0-5 °C. The pH of the reaction mixture was adjusted to 2-3 with 0.25 L of aqueous 1 M hydrochloric acid, followed by extraction with ethyl acetate (1 L x 2). The organic layers were combined and washed sequentially with 2.0 L of water and 2.0 L of saturated saline. The solvent was removed by distillation under reduced pressure (30-40 mmHg) to give 3-(2-methoxy-5-methylphenyl)-3-phenyl-1-propanol (yield: 0.462 kg, 97% yield). The purity of the product was >95% by HPLC analysis.

References

[1] Patent: WO2010/46801, 2010, A2. Location in patent: Page/Page column 16
[2] Patent: WO2010/92500, 2010, A2. Location in patent: Paragraph 157-164

3-(2-Methoxy-5-methylphenyl)-3-phenyl propanol(124937-73-1)Related Product Information

• Silicone oil (high temperature)
• 2-Amino-2-methyl-1-propanol
• Chlorodimethylphenylsilane
• Diphenyl ether
• 1-PHENYL-2-PROPANOL
• PHENYL VALERATE
• beta-Methylphenethyl alcohol
• 4-Methoxyphenylacetone
• Phenyl salicylate
• 1-Propanol
• 2-Methyl-1-propanol
• Tolterodine
• PHENYL RESIN
• Tolterodine EP Impurity D
• Tolterodine hydrobromide
• 2-Methoxy-5-methyl-N,N-bis(1-methylethyl)-3-phenylbenzenepropanamine fumarate
• Benzenepropanol, 2-hydroxy-5-methyl-γ-phenyl-, (γR)-
• Tolterodine EP Impurity G