2-[(Phenyl)methylene]-3-oxobutanoic acid, methyl ester

Base Information

• Chemical Name: 2-[(Phenyl)methylene]-3-oxobutanoic acid, methyl ester
• CAS No.: 15768-07-7
• Molecular Formula: C12H12 O3
• Molecular Weight: 204.225
• DSSTox Substance ID: DTXSID101020438
• Mol file: 15768-07-7.mol

Synonyms:methyl 2-acetyl-3-phenylacrylate;CBMicro_002289;Methyl 2-benzylideneacetoacetate;DQODZEKNJPJKED-UHFFFAOYSA-N;DTXSID101020438;2-[(phenyl)methylene]-3-oxobutanoic acid, methyl ester

Chemical Property of 2-[(Phenyl)methylene]-3-oxobutanoic acid, methyl ester

Chemical Property:

• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.552
• Boiling Point: 251.5°C at 760 mmHg
• Flash Point: 103°C
• PSA: 43.37000
• Density: 1.132g/cm³
• LogP: 1.83200
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 204.078644241
• Heavy Atom Count: 15
• Complexity: 273

Purity/Quality:

99.9% ^*data from raw suppliers

(E)-Methyl2-benzylidene-3-oxobutanoate 95+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 36/38-51/53
• Safety Statements: 26-37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=CC1=CC=CC=C1)C(=O)OC

Technology Process of 2-[(Phenyl)methylene]-3-oxobutanoic acid, methyl ester

There total 16 articles about 2-[(Phenyl)methylene]-3-oxobutanoic acid, methyl 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: 98.0%

benzaldehyde (100-52-7) + acetoacetic acid methyl ester (105-45-3) → methyl 2-benzylidene-3-oxobutanoate (15768-07-7)

Guidance literature:

With piperidine; acetic acid; In benzene; for 3h; Heating;

DOI:10.1016/S0040-4020(01)01173-5

Reference yield: 83.0%

(S)-2-((S)-Hydroxy-phenyl-methyl)-3-methoxy-but-3-enoic acid methyl ester → methyl 2-benzylidene-3-oxobutanoate (15768-07-7)

Guidance literature:

With hydrogenchloride; In methanol; for 8h; Ambient temperature;

DOI:10.1016/S0040-4039(99)00724-8

Reference yield: 75.0%

2,5-dimethyl-3-phenyl-4-carbomethoxy-4-isoxazoline (108817-72-7) → (E)-2-acetyl-1-phenyl-prop-1,2-enoic acid methyl ester (20048-06-0,15768-07-7,20048-05-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1016/S0040-4039(00)95872-6

upstream raw materials:

benzaldehyde

acetoacetic acid methyl ester

ethyl acetoacetate

2,5-dimethyl-3-phenyl-4-carbomethoxy-4-isoxazoline

Downstream raw materials:

2,5-dihydro-4-methyl-2-phenyl-1,5-benzothiazepine-3-carboxylic acid, methyl ester

3,3-Dimethoxy-2-[1-phenyl-meth-(Z)-ylidene]-butyric acid methyl ester

2,5-dihydro-1,1-dioxo-4-methyl-2-phenyl-1,5-benzothiazepine-3-carboxylic acid methyl ester

C₂₃H₂₇NO₄

Refernces

• 1、 Naikwadi, Dhanaji R.,Bankar, Balasaheb D.,Ravi, Krishnan,Biradar, Ankush V.. "Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds". . p. 3691 - 3703. Retrieved 2021/06/12.
• 2、 Rahmatpour, Ali,Goodarzi, Niloofar. "Cross-linked polystyrene-TiCl4 complex as a reusable Lewis acid catalyst for solvent-free Knoevenagel condensations of 1,3-dicarbonyl compounds with aldehydes". . p. 24 - 31. Retrieved 2019/03/08.