Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate

Base Information

• Chemical Name: Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate
• CAS No.: 82962-54-7
• Molecular Formula: C9H16O4
• Molecular Weight: 188.224
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40452100
• Nikkaji Number: J3.647.796B
• Wikidata: Q72469813
• Mol file: 82962-54-7.mol

Synonyms:Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate;82962-54-7;2,2-Dimethyl-[1,3]dioxane-5-carboxylic acid ethyl ester;2,2-DIMETHYL-5-CARBETHOXY-1,3-DIOXANE;MFCD11975772;1,3-Dioxane-5-carboxylic acid, 2,2-dimethyl-, ethyl ester;2,2-diMethyl-5-ethoxycarbonyl-1,3-dioxane;SCHEMBL1867430;DTXSID40452100;MYGMWHATZAFUIU-UHFFFAOYSA-N;AMY40724;CS-B1510;AKOS015918072;SB38910;DS-17340;SY114002;FT-0762264;Ethyl2,2-dimethyl-1,3-dioxane-5-carboxylate;J3.647.796B;EN300-179148;F12519;A856227;2,2-Dimethyl-1,3-dioxane-5-carboxylic acid ethyl ester

Chemical Property of Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate

Chemical Property:

• Boiling Point: 75℃ (0.4 Torr)
• Flash Point: 85.0±23.2℃
• PSA: 44.76000
• Density: 1.039±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 0.94860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 188.10485899
• Heavy Atom Count: 13
• Complexity: 178

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl2,2-Dimethyl-1,3-dioxane-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1COC(OC1)(C)C

Technology Process of Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate

There total 4 articles about Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate 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: 78.0%

2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester (51335-75-2) → 2,2-dimethyl-5-ethoxycarbonyl-1,3-dioxane (82962-54-7)

Guidance literature:

With water; sodium chloride; In dimethyl sulfoxide; for 20h; Reflux;

DOI:10.1055/s-0036-1588104

Reference yield: 65.0%

2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester (51335-75-2) → ethyl 2-(hydroxymethyl)acrylate (10029-04-6) + 2,2-dimethyl-5-ethoxycarbonyl-1,3-dioxane (82962-54-7)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; for 6h; Heating;

DOI:10.1016/S0040-4020(01)80939-X

Reference yield:

diethyl bis(hydroxymethyl)malonate (20605-01-0) → 2,2-dimethyl-5-ethoxycarbonyl-1,3-dioxane (82962-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / p-toluenesulfonic acid monohydrate / 5 h / Ambient temperature

2: 74 percent / aq. NaCl / dimethylsulfoxide / 24 h / 180 °C

With toluene-4-sulfonic acid; sodium chloride; In dimethyl sulfoxide;

DOI:10.1248/cpb.41.339

upstream raw materials:

2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester

diethyl bis(hydroxymethyl)malonate

2,2-dimethoxy-propane

Downstream raw materials:

2,2-dimethyl-5-hydroxymethyl-1,3-dioxane

5-iodomethyl-2,2-dimethyl-1,3-dioxane

5-(toluenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane

R_S-1-methyl-2-(2,2-dimethyl-1,2-dioxolanyl)-2-p-tolylsulfinyl-1-ethanone

Refernces

• 1、 Baranov, Mikhail S.,Kaskova, Zinaida M.,Gritсenko, Roman,Postikova, Svetlana G.,Ivashkin, Pavel E.,Kislukhin, Alexander A.,Moskvin, Dmitrii I.,Mineev, Konstantin S.,Arseniev, Alexander S.,Labas, Yulii A.,Yampolsky, Ilia V.. "Synthesis of Panal Terpenoid Core". supporting information. p. 583 - 588. Retrieved 2017/03/11.
• 2、 -. "METHODS AND COMPOSITIONS FOR THE SYNTHESIS OF MULTIMERIZING AGENTS". Page/Page column 16-17. . Retrieved 2012/08/08.