1-Methyl-2-(1-methylvinyl)cyclobutaneacetic acid

Base Information

• Chemical Name: 1-Methyl-2-(1-methylvinyl)cyclobutaneacetic acid
• CAS No.: 55760-16-2
• Molecular Formula: C10H16O2
• Molecular Weight: 168.236
• Mol file: 55760-16-2.mol

Synonyms:1-Methyl-2-(1-methylvinyl)cyclobutaneacetic acid

Chemical Property of 1-Methyl-2-(1-methylvinyl)cyclobutaneacetic acid

Chemical Property:

• PSA: 37.30000
• LogP: 2.45350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Methyl-2-(1-methylvinyl)cyclobutaneacetic acid

There total 20 articles about 1-Methyl-2-(1-methylvinyl)cyclobutaneacetic acid 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%

2-acetyl-1-methyl-1-cyclobutaneacetic acid (412011-51-9) + methyl-triphenylphosphonium iodide (2065-66-9) → 2-isopropenyl-1-methyl-1-cyclobutaneacetic acid (55760-16-2)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

2-acetyl-1-methyl-1-cyclobutaneacetic acid; In tetrahydrofuran; hexane; at 0 ℃; for 15h; Further stages.;

DOI:10.1021/jo000853+

Reference yield:

eucarvone (503-93-5) → cis-1-methyl-2-(1-methylethenyl)-cyclobutaneacetic acid (29578-30-1,53171-67-8,55760-16-2,68225-43-4,68225-44-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Irradiation

2: H₂ / Pd-C

3: (i) isopentyl nitrite, potassium 2-methyl-butan-2-olate, (ii) (heating), N₂H₄*H₂O, KOH

4: SOCl₂ / dimethylformamide

5: KOH / 200 °C

With potassium hydroxide; thionyl chloride; hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1139/v74-206

Reference yield:

1,4,4-Trimethyl-bicyclo<3.2.0>hepten-(6)-on-(2) → cis-1-methyl-2-(1-methylethenyl)-cyclobutaneacetic acid (29578-30-1,53171-67-8,55760-16-2,68225-43-4,68225-44-5)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd-C

2: (i) isopentyl nitrite, potassium 2-methyl-butan-2-olate, (ii) (heating), N₂H₄*H₂O, KOH

3: SOCl₂ / dimethylformamide

4: KOH / 200 °C

With potassium hydroxide; thionyl chloride; hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1139/v74-206

upstream raw materials:

2-acetyl-1-methyl-1-cyclobutaneacetic acid

methyl-triphenylphosphonium iodide

(trimethylsilyl)methylmagnesium chloride

cis-(+/-)-2-acetyl-1-methylcyclobutaneacetic acid

Downstream raw materials:

grandisol

trans-2-(1-methyl-2-(prop-1-en-2-yl)cyclobutyl)ethanol

Refernces

• 1、 Hamon,Tuck. "An asymmetric synthesis of (+)-grandisol, a constituent of the aggregation pheromone of the cotton boll weevil, via a kinetic resolution". . p. 7839 - 7846. Retrieved 2007/10/03.
• 2、 Yamazaki, Shoko,Fujitsuka, Hiroyuki,Takara, Fukumi,Inoue, Takashi. "Utilization of Selenium-directed Cycloadditions: Concise Synthesis of (+/-)-Fragranol". . p. 695 - 700. Retrieved 2007/10/02.