Methyl 3-hydroxy-3-phenylcyclobutane-1-carboxylate

Base Information

• Chemical Name: Methyl 3-hydroxy-3-phenylcyclobutane-1-carboxylate
• CAS No.: 69584-45-8
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.241
• DSSTox Substance ID: DTXSID20697476
• Nikkaji Number: J1.053.039C
• Mol file: 69584-45-8.mol

Synonyms:SB 22484;SB-22484;SB22484

Chemical Property of Methyl 3-hydroxy-3-phenylcyclobutane-1-carboxylate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CC(C1)(C2=CC=CC=C2)O

Technology Process of Methyl 3-hydroxy-3-phenylcyclobutane-1-carboxylate

There total 4 articles about Methyl 3-hydroxy-3-phenylcyclobutane-1-carboxylate 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: 76.0%

trans-3-hydroxy-3-phenylcyclobutane-1-carboxylic acid + methyl iodide (74-88-4) → methyl trans-3-hydroxy-3-phenylcyclobutanecarboxylate (69584-45-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201500746

Reference yield:

methyl 3-oxocyclobutanecarboxylate (695-95-4) + phenylmagnesium bromide → methyl trans-3-hydroxy-3-phenylcyclobutanecarboxylate (69584-45-8)

Guidance literature:

In diethyl ether; at -80 ℃;

Reference yield:

bromobenzene (108-86-1,52753-63-6) → methyl trans-3-hydroxy-3-phenylcyclobutanecarboxylate (69584-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide

With n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201500746

upstream raw materials:

methyl 3-oxocyclobutanecarboxylate

3-oxocyclobutanecarboxylic acid

bromobenzene

methyl iodide

Downstream raw materials:

cis-methyl 3-phenylcyclobutane-1-carboxylate

3-Cyclohexyl-cyclobutanecarboxylic acid

cis-3-phenylcyclobutanecarboxylic acid