1,3-Dioxolane-2,2-diacetic acid, diethyl ester

Base Information

• Chemical Name: 1,3-Dioxolane-2,2-diacetic acid, diethyl ester
• CAS No.: 71022-90-7
• Molecular Formula: C₁₁H₁₈O₆
• Molecular Weight: 246.26
• Hs Code.: 2932999099
• NSC Number: 120373
• DSSTox Substance ID: DTXSID10298037
• Wikidata: Q82039607
• Mol file: 71022-90-7.mol

Synonyms:71022-90-7;1,3-Dioxolane-2,2-diacetic acid, diethyl ester;1,3-DIOXOLANE-2,2-DIACETIC ACID DIETHYL ESTER;diethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate;ethyl 2-[2-(2-ethoxy-2-oxoethyl)-1,3-dioxolan-2-yl]acetate;diethyl2,2'-(1,3-dioxolane-2,2-diyl)diacetate;NSC120373;SCHEMBL16204253;DTXSID10298037;WCA02290;AB3689;MFCD09953117;NSC-120373;AS-44728

Chemical Property of 1,3-Dioxolane-2,2-diacetic acid, diethyl ester

Chemical Property:

• Boiling Point: 300.5°Cat760mmHg
• Flash Point: 127.9°C
• PSA: 71.06000
• Density: 1.132g/cm³
• LogP: 0.63590
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 246.11033829
• Heavy Atom Count: 17
• Complexity: 247

Purity/Quality:

99.3% ^*data from raw suppliers

1,3-Dioxolane-2,2-diaceticAcidDiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1(OCCO1)CC(=O)OCC

Technology Process of 1,3-Dioxolane-2,2-diacetic acid, diethyl ester

There total 2 articles about 1,3-Dioxolane-2,2-diacetic acid, diethyl 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: 93.0%

ethylene glycol (107-21-1) + diethyl 1,3-acetonedicarboxylate (105-50-0) → diethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate (71022-90-7)

Guidance literature:

With toluene-4-sulfonic acid; for 5h; Reflux; Dean-Stark;

DOI:10.1016/j.ejmech.2013.02.029

Reference yield:

→ diethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate (71022-90-7)

Guidance literature:

γ-Keto-pimelinsaeure-aethylester, p-Toluolsulfonsaeure, Aethylenglykol in Bzl., Δ;

Reference yield:

diethyl 2,2'-(1,3-dioxolane-2,2-diyl)diacetate (71022-90-7) → (3R,6R,9S)-2-oxo-3-amino-(N-benzyloxycarbonyl)-9-(methoxycarbonyl)-1-azabicyclo[4.3.0]nonane

Guidance literature:

Multi-step reaction with 5 steps

1.1: 70 percent Spectr_. / DIBAL / toluene / 1.17 h / -78 °C

2.1: 72 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

3.1: 95 percent / H₂ / Rh(I)(COD)(R,R) Et-DUPHOS / methanol / 24 h / 3620.04 Torr

4.1: H₂ / 10 percent Pd/C / methanol; aq. HCl / 24 h / 3620.04 Torr

4.2: NaHCO₃ / dioxane; H₂O / 4 h / pH 8 - 9

4.3: 74 percent / dioxane; H₂O / 3 h

5.1: 74 percent / NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -50 - -20 °C

With hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; Rh(I)(COD)(R,R)-Et-DUPHOS; In tetrahydrofuran; hydrogenchloride; methanol; dichloromethane; toluene; 2.1: Horner-Emmons olefination;

DOI:10.1016/S0040-4039(01)00409-9

upstream raw materials:

ethylene glycol

diethyl 1,3-acetonedicarboxylate

Downstream raw materials:

2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol

2,2'-(1,3-dioxolane-2,2-diyl)diacetic acid

ethyl 3,3-(ethylenedioxy)-4-formylbutyrate

1,3-DIOXOLANE-2,2-DIACETALDEHYDE

Refernces

• 1、 -. "HETEROCYCLIC COMPOUNDS AS INHIBITORS OF HPK1". Page/Page column 203. . Retrieved 2021/01/29.
• 2、 -. "DEUTERATED DIAMINOPYRIMIDINE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SUCH COMPOUNDS". Paragraph 0097; 0103. . Retrieved 2016/05/09.