(2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate

Base Information

• Chemical Name: (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate
• CAS No.: 107053-60-1
• Molecular Formula: C₂₃H₃₆O₄S
• Molecular Weight: 408.602
• Mol file: 107053-60-1.mol

Synonyms:(2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate

Chemical Property of (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate

There total 4 articles about (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate 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: 88.0%

(-)-2-methylene-1-(hydroxymethyl)cyclotetradecan-1-ol (107081-66-3) + p-toluenesulfonyl chloride (98-59-9) → (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate (107053-60-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00382a024

Reference yield:

ethyl (E)-2-methylcyclotetradecenecarboxylate (107053-56-5) → (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate (107053-60-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / i-Bu₂AlH / hexane / 2 h / -78 °C

2: 1.) (i-PrO)4Ti, (+)-diethyl tartrate, t-BuOOH, 2.) H₂O / 1.) CH₂Cl₂, -23 deg C to -30 deg C, 20 h, 2.) CH₂Cl₂, acetone, -23 deg C to RT, 2.75 h

3: 2,2,6,6-tetramethylpiperidine, n-BuLi, Et₂AlCl / benzene; hexane / 5 h / 0 °C

4: 88 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0 °C

With 2,2,6,6-tetramethyl-piperidine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; water; diethylaluminium chloride; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; triethylamine; In hexane; dichloromethane; benzene;

DOI:10.1021/jo00382a024

Reference yield:

(1S,2S)-(2-methyl-1,2-epoxycyclotetradecyl)methanol (107132-45-6) → (2-methylene-1-hydroxy-1-cyclotetradecyl)methyl p-toluenesulfonate (107053-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2,6,6-tetramethylpiperidine, n-BuLi, Et₂AlCl / benzene; hexane / 5 h / 0 °C

2: 88 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0 °C

With 2,2,6,6-tetramethyl-piperidine; dmap; n-butyllithium; diethylaluminium chloride; triethylamine; In hexane; dichloromethane; benzene;

DOI:10.1021/jo00382a024

upstream raw materials:

(-)-2-methylene-1-(hydroxymethyl)cyclotetradecan-1-ol

p-toluenesulfonyl chloride

ethyl (E)-2-methylcyclotetradecenecarboxylate

(1S,2S)-(2-methyl-1,2-epoxycyclotetradecyl)methanol