(2R,3R)-3-(4-Methylphenyl)-1,2-butanediol

Base Information

• Chemical Name: (2R,3R)-3-(4-Methylphenyl)-1,2-butanediol
• CAS No.: 122058-31-5
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• DSSTox Substance ID: DTXSID001270402
• Mol file: 122058-31-5.mol

Synonyms:(2R,3R)-3-(4-Methylphenyl)-1,2-butanediol;DTXSID001270402;122058-31-5

Chemical Property of (2R,3R)-3-(4-Methylphenyl)-1,2-butanediol

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 180.115029749
• Heavy Atom Count: 13
• Complexity: 139

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of (2R,3R)-3-(4-Methylphenyl)-1,2-butanediol

There total 3 articles about (2R,3R)-3-(4-Methylphenyl)-1,2-butanediol 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: 73.0%

lithium dimethylcyanocuprate + (-)-3-(p-tolyl)glycidol → (2R,3R)-3-p-Tolyl-butane-1,2-diol (122058-31-5)

Guidance literature:

In diethyl ether; at -40 ℃; for 1.5h;

DOI:10.1039/c39880001538

Reference yield:

p-methylcinnamyl alcohol (122058-30-4) → (2R,3R)-3-p-Tolyl-butane-1,2-diol (122058-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / L-(+)-DIPT, Ti(OiPr)4, t-BuOOH / CH₂Cl₂ / 34 h / -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In dichloromethane;

DOI:10.1039/c39880001538

Reference yield:

trimethylaluminum (75-24-1) + (-)-3-(p-tolyl)glycidol → (2R,3S)-3-p-Tolyl-butane-1,2-diol (122058-32-6) + (2R,3R)-3-p-Tolyl-butane-1,2-diol (122058-31-5)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1039/c39880001538

upstream raw materials:

trimethylaluminum

p-methylcinnamyl alcohol

Downstream raw materials:

2-(4-methylphenyl)propanal