Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester

Base Information

• Chemical Name: Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester
• CAS No.: 623936-71-0
• Molecular Formula: C12H15BrO3
• Molecular Weight: 287.153
• DSSTox Substance ID: DTXSID90479307
• Nikkaji Number: J2.137.005C
• Wikidata: Q82313292
• Mol file: 623936-71-0.mol

Synonyms:623936-71-0;Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester;DTXSID90479307

Chemical Property of Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 286.02046
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1CCBr)C)C(=O)OC)O

Technology Process of Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester

There total 2 articles about Benzoic acid, 3-(2-bromoethyl)-6-hydroxy-2,4-dimethyl-, methyl ester 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: 94.0%

8-hydroxy-4,8-dimethyl-6-oxo-spiro[2.5]oct-4-ene-5-carboxylic acid methyl ester (716381-20-3) → methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate (623936-71-0)

Guidance literature:

With titanium(IV) bromide; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.bmc.2006.03.037

Reference yield: 82.0%

1,1-diacetylcyclopropane (695-70-5) + 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1,81114-98-9,67609-52-3) → methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate (623936-71-0)

Guidance literature:

With titanium(IV) bromide; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo0485278

Reference yield: 90.0%

trifluoromethylsulfonic anhydride (358-23-6) + methyl 3-(2-bromoethyl)-6-hydroxy-2,4-dimethylbenzoate (623936-71-0) → [2-(methoxycarbonyl)-4-(2-bromoethyl)-3,5-dimethylphenyl] trifluoromethanesulfonate (846541-12-6)

Guidance literature:

In pyridine; at -78 - 10 ℃;

DOI:10.1016/j.tetlet.2004.12.030

upstream raw materials:

1,1-diacetylcyclopropane

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

8-hydroxy-4,8-dimethyl-6-oxo-spiro[2.5]oct-4-ene-5-carboxylic acid methyl ester

Downstream raw materials:

[2-(methoxycarbonyl)-4-(2-bromoethyl)-3,5-dimethylphenyl] trifluoromethanesulfonate