Methyl 3,5-dioxohexanoate

Base Information

• Chemical Name: Methyl 3,5-dioxohexanoate
• CAS No.: 29736-80-9
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID00337065
• Nikkaji Number: J145.263K
• Wikidata: Q72490317
• Mol file: 29736-80-9.mol

Synonyms:Methyl 3,5-dioxohexanoate;29736-80-9;3,5-Dioxo-hexanoic acid methyl ester;Hexanoic acid, 3,5-dioxo-, methyl ester;MFCD12547105;Methyl3,5-dioxohexanoate;SCHEMBL3585736;DTXSID00337065;AMY17189;AKOS015851473;DS-16555;SY108603;A5518;CS-0137250;FT-0757632;C74527;2-(2-Chloroethyl)-1,2,3,4,5,6-hexahydrobenzo[c]azocine hydrochloride

Chemical Property of Methyl 3,5-dioxohexanoate

Chemical Property:

• Boiling Point: 221.6 °C at 760 mmHg
• PKA: 7.72±0.10(Predicted)
• Flash Point: 89.8 °C
• PSA: 60.44000
• Density: 1.115 g/cm³
• LogP: 0.09770
• Storage Temp.: 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

99%, ^*data from raw suppliers

Methyl3,5-dioxohexanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)CC(=O)OC

Technology Process of Methyl 3,5-dioxohexanoate

There total 4 articles about Methyl 3,5-dioxohexanoate 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: 44.0%

(Z)-5-Hydroxy-3-oxo-6-((R)-toluene-4-sulfinyl)-hex-4-enoic acid methyl ester → 3,5-dioxohexanoic acid methyl ester (29736-80-9) + di(p-tolyl) disulfide (103-19-5) + (+)-<5(S),S(R)> methyl 3-oxo-5-hydroxy-6-(p-tolylsulfinyl) hexanoate (171523-67-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; methanol; toluene; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(03)00125-3

Reference yield: 30.0%

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1) + acetyl chloride (75-36-5) → 3,5-dioxohexanoic acid methyl ester (29736-80-9) + acetoacetic acid methyl ester (105-45-3)

Guidance literature:

In diethyl ether; at -78 ℃; for 4h; Yields of byproduct given;

Reference yield: 18.0%

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (771-03-9) → 4-hydroxy-6-methyl-2-pyron (675-10-5) + 3,5-dioxohexanoic acid methyl ester (29736-80-9) + acetoacetic acid methyl ester (105-45-3)

Guidance literature:

With sodium methylate; In methanol; benzene; for 18h; Heating;

upstream raw materials:

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

acetyl chloride

methanol

2,7-dimethyl-4H-pyrano<3,2-c>-2H-pyran-4,5-dione

Downstream raw materials:

7-Hydroxy-3,5-dioxo-7,7-diphenyl-heptanoic acid methyl ester

methyl orsellinate

(6R)-6-methyl-5,6-dihydro-2H-pyran-2-one

(S)-parasorbic acid

Refernces

• 1、 Crombie, Leslie,Games, David E.,James, Alun W. G.. "Reactions of fused and unfused α-pyrones with magnesium alkoxide, sodium alkoxide and water as the nucleophile: effects of chelation". . p. 2715 - 2724. Retrieved 2007/10/03.