1,3-Dioxolane-2-propanoic acid, 2-methyl-, methyl ester

Base Information

• Chemical Name: 1,3-Dioxolane-2-propanoic acid, 2-methyl-, methyl ester
• CAS No.: 35351-33-8
• Molecular Formula: C8H14O4
• Molecular Weight: 174.197
• DSSTox Substance ID: DTXSID301267870
• Nikkaji Number: J113.614C
• Mol file: 35351-33-8.mol

Synonyms:1,3-Dioxolane-2-propanoic acid, 2-methyl-, methyl ester;35351-33-8;Methyl levulinate ethylene ketal;SCHEMBL7847493;DTXSID301267870;Methyl 4-oxopentanoate ethyleneketal;methyl 2-methyl-l,3-dioxolane-2-propionate;Methyl 2-methyl-1,3-dioxolane-2-propanoate;2-Methyl-1,3-dioxolane-2-propanoic acid methyl ester;Methyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate #

Chemical Property of 1,3-Dioxolane-2-propanoic acid, 2-methyl-, methyl ester

Chemical Property:

• PSA: 44.76000
• LogP: 0.70260
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCCO1)CCC(=O)OC

Technology Process of 1,3-Dioxolane-2-propanoic acid, 2-methyl-, methyl ester

There total 9 articles about 1,3-Dioxolane-2-propanoic acid, 2-methyl-, 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: 95.0%

levulinic acid methyl ester (624-45-3) + ethylene glycol (107-21-1) → methyl 3‐(2‐methyl‐1,3‐dioxolan‐2‐yl)propanoate (35351-33-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 16h; Reflux; Dean-Stark;

DOI:10.1002/chem.201902917

Reference yield:

levulinic acid (123-76-2) → methyl 3‐(2‐methyl‐1,3‐dioxolan‐2‐yl)propanoate (35351-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / IR-120 H⁺ resin

2: 78 percent / TsOH / benzene

With IR-120 H⁺ resin; toluene-4-sulfonic acid; In benzene;

DOI:10.1021/jo9822838

Reference yield:

Ethyl levulinate ethylene ketal (941-43-5) → methyl 3‐(2‐methyl‐1,3‐dioxolan‐2‐yl)propanoate (35351-33-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1 N NaOH / H₂O

2: 1.) N,N'-carbonyldiimidazole / 1.) THF, 1 h; 2.) 30 min

3: 1.) 1.6 M butyllithium / 1.) hexane, THF, -78 deg C, 10 min; 2.) 30 min

4: 1.) 1.6 M n-butyllithium / 1.) hexane, THF, r.t., 2 h; 2.) 60 deg C, 2 h

5: triethylamine / hexane; tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; n-butyllithium; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; hexane; water;

upstream raw materials:

2-methyl-1,3-dioxolane

acrylic acid methyl ester

methanol

levulinic acid methyl ester

Downstream raw materials:

Methyl (+/-)-2-hydroxy-3-(2-methyl-1,3-dioxolan-2-yl)propanoate

methyl 4-oxo-2-(2-phenyl-2-propenyl)pentanoate ethylene ketal

methyl 4-oxo-2-(2-oxo-2-phenylethyl)pentanoate ethylene ketal

1-diazo-3-(2-oxo-2-phenylethyl)hexane-2,5-dione

Refernces

• 1、 Wong, Jeff Y. F.,Tobin, John M.,Vilela, Filipe,Barker, Graeme. "Batch Versus Flow Lithiation–Substitution of 1,3,4-Oxadiazoles: Exploitation of Unstable Intermediates Using Flow Chemistry". supporting information. p. 12439 - 12445. Retrieved 2019/09/06.
• 2、 Wu, Yikang,Li, Yan,Wu, Yu-Lin. "Tandem hemiketal formation-intramolecular Friedel-Crafts alkylation: A facile route to hetero-atom-substituted benzo-fused bicyclo[3.3.1]nonanes". . p. 163 - 171. Retrieved 2007/10/03.