Diethyl 3-hydroxy-3-methylglutarate

Base Information

• Chemical Name: Diethyl 3-hydroxy-3-methylglutarate
• CAS No.: 73489-84-6
• Molecular Formula: C10H18O5
• Molecular Weight: 218.25
• Hs Code.: 29171900
• European Community (EC) Number: 277-481-0
• DSSTox Substance ID: DTXSID30994246
• Nikkaji Number: J295.229G
• Wikidata: Q82985107
• ChEMBL ID: CHEMBL156298
• Mol file: 73489-84-6.mol

Synonyms:Diethyl 3-hydroxy-3-methylglutarate;73489-84-6;diethyl 3-hydroxy-3-methylpentanedioate;EINECS 277-481-0;CHEMBL156298;DTXSID30994246;FT-0718710;3-Hydroxy-3-methylpentanedioic acid diethyl ester

Chemical Property of Diethyl 3-hydroxy-3-methylglutarate

Chemical Property:

• Vapor Pressure: 6.77E-05mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 307.3 °C at 760 mmHg
• Flash Point: 111.3 °C
• PSA: 72.83000
• Density: 1.101 g/cm³
• LogP: 0.64380
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 218.11542367
• Heavy Atom Count: 15
• Complexity: 204

Purity/Quality:

98%Min ^*data from raw suppliers

3-HYDROXY-3-METHYL-GLUTARIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(C)(CC(=O)OCC)O

Technology Process of Diethyl 3-hydroxy-3-methylglutarate

There total 4 articles about Diethyl 3-hydroxy-3-methylglutarate 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:

meglutol (503-49-1) + ethyl iodide (75-03-6) → 3-hydroxy-3-methyl-glutaric acid diethyl ester (73489-84-6)

Guidance literature:

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

DOI:10.1021/jm50001a011

Reference yield:

1,1-diallylethanol (25201-40-5) → 3-hydroxy-3-methyl-glutaric acid diethyl ester (73489-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) ozone, 2.) AcOH, aq. H₂SO₄, 30percent aq. H₂O₂ / 1.) CH₂Cl₂, ethyl acetate, -60 deg C to -30 deg C, 1 h, 2.) ethyl acetate, reflux, 2 h

2: K₂CO₃ / dimethylformamide / 16 h / 20 °C

With sulfuric acid; dihydrogen peroxide; potassium carbonate; ozone; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm50001a011

Reference yield:

ethyl acetoacetate (141-97-9) + chloroacetic acid ethyl ester (105-39-5) → 3-hydroxy-3-methyl-glutaric acid diethyl ester (73489-84-6)

Guidance literature:

With copper; zinc; benzene;

DOI:10.1021/ja01106a028 DOI:10.3758/BF03195781

upstream raw materials:

ethyl acetoacetate

chloroacetic acid ethyl ester

ethyl bromoacetate

meglutol

Downstream raw materials:

meglutol

3-methyl-pentenedioic acid anhydride

3-acetoxy-3-methylpentane-1,5-dioic acid anhydride

Refernces