Ethyl 3-hydroxy-2,2,4-trimethylpentanoate

Base Information

• Chemical Name: Ethyl 3-hydroxy-2,2,4-trimethylpentanoate
• CAS No.: 7403-65-8
• Molecular Formula: C10H20 O3
• Molecular Weight: 188.267
• NSC Number: 54809
• DSSTox Substance ID: DTXSID50288230
• ChEMBL ID: CHEMBL2001295
• Mol file: 7403-65-8.mol

Synonyms:ethyl 3-hydroxy-2,2,4-trimethylpentanoate;7403-65-8;NSC54809;3-Hydroxy-2,2,4-trimethylvaleric Acid Ethyl Ester;NSC-54809;starbld0033139;CHEMBL2001295;SCHEMBL13256822;DTXSID50288230;AKOS011685536;NCI60_004350

Chemical Property of Ethyl 3-hydroxy-2,2,4-trimethylpentanoate

Chemical Property:

• Vapor Pressure: 0.00184mmHg at 25°C
• Boiling Point: 259.8°C at 760 mmHg
• PKA: 14.18±0.20(Predicted)
• Flash Point: 98.4°C
• PSA: 46.53000
• Density: 0.963g/cm³
• LogP: 1.59260
• Solubility.: DCM, Ether, Ethyl Acetate
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 188.14124450
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-2,2,4-trimethylvalericAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C)C(C(C)C)O
• Uses: 3-Hydroxy-2,2,4-trimethylvaleric Acid Ethyl Ester is a urinary metabolite of the plasticizer 2,2,4-trimethyl-1,3-pentanediol Diisobutyrate (T798120).

Technology Process of Ethyl 3-hydroxy-2,2,4-trimethylpentanoate

There total 6 articles about Ethyl 3-hydroxy-2,2,4-trimethylpentanoate 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: 82.0%

ethyl 2-bromoisobutyrate (600-00-0) + isobutyraldehyde (78-84-2) → ethyl 2,2,4-trimethyl-3-hydroxyvalerate (7403-65-8)

Guidance literature:

ethyl 2-bromoisobutyrate; isobutyraldehyde; With bis(cyclopentadienyl)titanium dichloride; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene; In tetrahydrofuran; at 20 ℃; for 14h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; Inert atmosphere;

DOI:10.1021/ja501313s

Reference yield:

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene (31469-16-6) + Ethyl isobutyrate (97-62-1) → 2-methyl-propan-1-ol (78-83-1) + ethyl 2,2,4-trimethyl-3-hydroxyvalerate (7403-65-8)

Guidance literature:

With boron trifluoride diethyl etherate; diisobutylaluminium hydride; Yield given. Multistep reaction; 1) CH₂Cl₂/toluene, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C, 1 h;

DOI:10.1021/jo00027a001

Reference yield:

ethanol (64-17-5) + 2,2,4-trimethyl-3-hydroxyvaleric acid (35763-45-2) → ethyl 2,2,4-trimethyl-3-hydroxyvalerate (7403-65-8)

Guidance literature:

With sulfuric acid; at 60 - 140 ℃; for 31h; Reagent/catalyst; Temperature;

upstream raw materials:

ethyl 2-bromoisobutyrate

isobutyraldehyde

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene

Ethyl isobutyrate

Downstream raw materials:

2,2,4-trimethyl-pent-3-en-1-ol

2,2,4-trimethyl-pent-3-enal

2,3,4-trimethyl-pentanal

2,4-dimethyl-2-pentene

Refernces

• 1、 Saito, Teruhiko,Nishiyama, Haruka,Tanahashi, Hiromasa,Kawakita, Kento,Tsurugi, Hayato,Mashima, Kazushi. "1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes as strong salt-free reductants for generating low-valent early transition metals with electron-donating ligands". supporting information. p. 5161 - 5170. Retrieved 2014/04/17.
• 2、 Bieber, Lothar W.,Malvestiti, Ivani,Storch, Elisabeth C.. "Reformatsky Reaction in Water: Evidence for a Radical Chain Process". . p. 9061 - 9064. Retrieved 2007/10/03.