(+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2-METHYL-2-PHENYL-1,3-DIOXOLANE

Base Information

• Chemical Name: (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2-METHYL-2-PHENYL-1,3-DIOXOLANE
• CAS No.: 109306-21-0
• Molecular Formula: C36H32 O4
• Molecular Weight: 528.64
• Mol file: 109306-21-0.mol

Synonyms:1,3-Dioxolane-4,5-dimethanol,2-methyl-a,a,a',a',2-pentaphenyl-, (4R,5R)- (9CI);1,3-Dioxolane-4,5-dimethanol, 2-methyl-a,a,a',a',2-pentaphenyl-, [4R-(2a,4a,5b)]-; (4R,5R)-2-Methyl-a,a,a',a',2-pentaphenyl-1,3-dioxolane-4,5-dimethanol

Chemical Property of (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2-METHYL-2-PHENYL-1,3-DIOXOLANE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 120 °C
• Refractive Index: 1.637
• Boiling Point: 701.941°C at 760 mmHg
• PKA: 12.28±0.29(Predicted)
• Flash Point: 378.32°C
• PSA: 58.92000
• Density: 1.221g/cm³
• LogP: 6.51550

Purity/Quality:

97% ^*data from raw suppliers

(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2-methyl-2-phenyl-1,3-dioxolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2-methyl-2-phenyl-1,3-dioxolane (CAS# 109306-21-0) is a TADDOL (α,α,α'',α''-tetraaryl-2,2-disubstituted 1,3-dioxolane-4,5-dimethanol) and is a chiral building block used in the perparation of optically active organotin derivatives. Via Ni catalyzation, (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2-methyl-2-phenyl-1,3-dioxolane has been used in the cycloisomerization of dienes.

Technology Process of (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2-METHYL-2-PHENYL-1,3-DIOXOLANE

There total 5 articles about (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2-METHYL-2-PHENYL-1,3-DIOXOLANE 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: 60.0%

phenylmagnesium bromide + (4R,5R)-2-phenyl-2-methyl-4,5-bis(methoxycarbonyl)-1,3-dioxolane (104333-83-7) → (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol (109306-21-0)

Guidance literature:

In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1246/bcsj.61.4379

Reference yield: 60.0%

(4R,5R)-2-phenyl-2-methyl-4,5-bis(methoxycarbonyl)-1,3-dioxolane (104333-83-7) + phenylmagnesium bromide (100-58-3) → (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol (109306-21-0)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04345

Reference yield:

acetophenone dimethyl acetal (4316-35-2) → (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol (109306-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / p-toluenesulfonic acid / benzene / Heating

2: 60 percent / tetrahydrofuran / 4 h / Ambient temperature

With toluene-4-sulfonic acid; In tetrahydrofuran; benzene;

DOI:10.1246/bcsj.61.4379

upstream raw materials:

(4R,5R)-2-phenyl-2-methyl-4,5-bis(methoxycarbonyl)-1,3-dioxolane

bromobenzene

acetophenone dimethyl acetal

phenylmagnesium bromide

Downstream raw materials:

isopropyl alcohol

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