4-(3-HYDROXY-3-METHYLBUT-1-YNYL)BENZOIC ACID METHYL ESTER

Base Information

• Chemical Name: 4-(3-HYDROXY-3-METHYLBUT-1-YNYL)BENZOIC ACID METHYL ESTER
• CAS No.: 33577-98-9
• Molecular Formula: C13H14 O3
• Molecular Weight: 218.252
• Hs Code.: 2918290000
• Mol file: 33577-98-9.mol

Synonyms:Benzoicacid, 4-(3-hydroxy-3-methyl-1-butynyl)-, methyl ester (9CI); Benzoic acid,p-(3-hydroxy-3-methyl-1-butynyl)-, methyl ester (8CI)

Chemical Property of 4-(3-HYDROXY-3-METHYLBUT-1-YNYL)BENZOIC ACID METHYL ESTER

Chemical Property:

• Vapor Pressure: 3.83E-05mmHg at 25°C
• Boiling Point: 338.4°Cat760mmHg
• Flash Point: 140.3°C
• PSA: 46.53000
• Density: 1.15g/cm³
• LogP: 1.59560

Purity/Quality:

98%Min ^*data from raw suppliers

methyl4-(3-hydroxy-3-methylbut-1-ynyl)benzoate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(3-HYDROXY-3-METHYLBUT-1-YNYL)BENZOIC ACID METHYL ESTER

There total 4 articles about 4-(3-HYDROXY-3-METHYLBUT-1-YNYL)BENZOIC ACID 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: 100.0%

methyl 4-iodobenzoate (619-44-3) + 2-methyl-but-3-yn-2-ol (115-19-5) → methyl 4-(3-hydroxy-3-methylbut-1-ynyl)benzoate (33577-98-9)

Guidance literature:

With copper(l) iodide; (Ph₃)2PdCl₂; triphenylphosphine; triethylamine; for 68h; Heating;

DOI:10.1021/jm030438k

Reference yield: 98.0%

4-methoxycarbonylphenyl bromide (619-42-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → methyl 4-(3-hydroxy-3-methylbut-1-ynyl)benzoate (33577-98-9)

Guidance literature:

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; for 0.666667h; Heating;

DOI:10.1021/jo00051a063

Reference yield:

4-Bromobenzoic acid (586-76-5) → methyl 4-(3-hydroxy-3-methylbut-1-ynyl)benzoate (33577-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 24 h / Reflux; Inert atmosphere

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / 18 h / 50 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sulfuric acid; triethylamine; triphenylphosphine; 2: Sonogashira coupling;

DOI:10.1002/pola.24442

upstream raw materials:

4-methoxycarbonylphenyl bromide

2-methyl-but-3-yn-2-ol

methyl 4-iodobenzoate

4-Bromobenzoic acid

Downstream raw materials:

4-Ethynyl-benzoic acid

4-ethynylbenzoic acid methyl ester

pentafluorophenyl 4-ethynylbenzoate

4-ethynylbenzoyl chloride

Refernces

• 1、 Nanubolu, Jagadeesh Babu,Reddy Singam, Maneesh Kumar,Sridhar Reddy, Maddi,Suresh, Vavilapalli,Suri Babu, Undamatla. "Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones". supporting information. p. 7888 - 7893. Retrieved 2021/10/25.
• 2、 Qiao, Hong,Zhang, Shengjun,Li, Kangkang,Cao, Zhengqiang,Zeng, Fanlong. "Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines". . p. 10843 - 10851. Retrieved 2019/09/12.