Ethanol, 2-(cyclopropyloxy)-, 4-methylbenzenesulfonate

Base Information

• Chemical Name: Ethanol, 2-(cyclopropyloxy)-, 4-methylbenzenesulfonate
• CAS No.: 862728-59-4
• Molecular Formula: C12H16O4S
• Molecular Weight: 256.323
• Hs Code.: 2930909899
• Mol file: 862728-59-4.mol

Synonyms:

Chemical Property of Ethanol, 2-(cyclopropyloxy)-, 4-methylbenzenesulfonate

Chemical Property:

• PSA: 60.98000
• LogP: 2.96010

Purity/Quality:

99% ^*data from raw suppliers

2-Cyclopropoxyethyl4-methylbenzenesulfonate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethanol, 2-(cyclopropyloxy)-, 4-methylbenzenesulfonate

There total 2 articles about Ethanol, 2-(cyclopropyloxy)-, 4-methylbenzenesulfonate 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-(cyclopropyloxy)ethan-1-ol (20117-44-6) + p-toluenesulfonyl chloride (98-59-9) → 2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate (862728-59-4)

Guidance literature:

2-(cyclopropyloxy)ethan-1-ol; With sodium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; water; at -5 - 0 ℃; for 1h; Inert atmosphere;

p-toluenesulfonyl chloride; In tetrahydrofuran; water; at 0 - 5 ℃; for 5h; Solvent; Temperature; Inert atmosphere;

Reference yield:

2-bromo-2-(2-ethyl)dioxolane (18742-02-4) → 2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate (862728-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iodine; magnesium / tetrahydrofuran / 10 h / 30 - 50 °C / Inert atmosphere

1.2: 30 h / 40 - 50 °C

1.3: brine / 2 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydroxide / water; tetrahydrofuran; 2-methyltetrahydrofuran / 24 h / 0 - 5 °C

With iodine; magnesium; sodium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; water; 1.1: |Grignard Reaction;

Reference yield: 81.0%

4-(5-bromo-2-chlorobenzyl)phenol (864070-18-8) + 2-(cyclopropyloxy)ethyl-4-methylbenzenesulfonate (862728-59-4) → 4-bromo-1-chloro-2-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]benzene (1118567-45-5)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.6b01818

upstream raw materials:

2-(cyclopropyloxy)ethan-1-ol

p-toluenesulfonyl chloride

2-bromo-2-(2-ethyl)dioxolane

Downstream raw materials:

4-bromo-1-chloro-2-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]benzene

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

1-chloro-2-(4-(2-cyclopropoxyethoxy)benzyl)-4-iodobenzene

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[[4-[2-(cyclopropyloxy)ethoxy]phenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxytetrahydropyran-3,4,5-triol

Refernces

• 1、 -. "Glucopyranosyl derivative and application thereof in medicines". Paragraph 0178; 0183; 0184; 0185. . Retrieved 2016/10/08.
• 2、 -. "PREPARATION OF HYDROXY-BENZYLBENZENE DERIVATIVES". Paragraph 0156-0158. . Retrieved 2015/04/28.