4-Ethoxy-4-oxo-1-phenylbut-2-ene-1-sulfonic acid

Base Information

• Chemical Name: 4-Ethoxy-4-oxo-1-phenylbut-2-ene-1-sulfonic acid
• CAS No.: 89295-32-9
• Molecular Formula: C12H14 O4 S
• Molecular Weight: 254.307
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID00699796
• Mol file: 89295-32-9.mol

Synonyms:DTXSID00699796;4-ethoxy-4-oxo-1-phenylbut-2-ene-1-sulfonic acid

Chemical Property of 4-Ethoxy-4-oxo-1-phenylbut-2-ene-1-sulfonic acid

Chemical Property:

• PSA: 68.82000
• LogP: 2.66040
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 270.05619472
• Heavy Atom Count: 18
• Complexity: 387

Purity/Quality:

98%min ^*data from raw suppliers

ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC(C1=CC=CC=C1)S(=O)(=O)O
• Uses: Ethyl 2-((phenylsulfonyl)methyl)acrylate can be used in the synthesis of ethyl 2-{[(1s,2r,3r,5s)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methyl}acrylate that it is radical allylation of b-alkylcatecholboranes.

Technology Process of 4-Ethoxy-4-oxo-1-phenylbut-2-ene-1-sulfonic acid

There total 6 articles about 4-Ethoxy-4-oxo-1-phenylbut-2-ene-1-sulfonic acid 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: 95.0%

sodium benzenesulfonate (873-55-2) + ethyl 2-bromomethyl-2-propenoate (17435-72-2) → 2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone (89295-32-9)

Guidance literature:

With PEO 400 (polyethylene oxide 400); In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1080/00397919108016422

Reference yield: 38.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + sodium benzenesulfonate (873-55-2) + ethyl acrylate (140-88-5,9003-32-1) → 2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone (89295-32-9)

Guidance literature:

formaldehyd; ethyl acrylate; With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; water; for 16h; Inert atmosphere;

With phosphorus tribromide; In diethyl ether; at -10 - 20 ℃; for 4h; Inert atmosphere;

sodium benzenesulfonate; In methanol; for 16h; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02273

Reference yield:

ethyl acrylate (140-88-5,9003-32-1) → 2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone (89295-32-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,4-diaza-bicyclo[2.2.2]octane / 1,4-dioxane; water / Inert atmosphere

2: phosphorus tribromide / diethyl ether / 3 h / -10 - 20 °C

3: methanol / 2.5 h / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; phosphorus tribromide; In 1,4-dioxane; methanol; diethyl ether; water;

DOI:10.1002/anie.201510014

upstream raw materials:

sodium benzenesulfonate

ethyl 2-bromomethyl-2-propenoate

ethyl acrylate

ethyl 2-(hydroxymethyl)acrylate

Downstream raw materials:

methylene-2 (oxo-2 cyclohexane)yl-3 propionate d'ethyle

ethyl 2-phenethylpropenoate

cis-Ethyl 2-methylene-3-(3'methyl-2'-oxocyclohexyl)propanoate

trans-Ethyl 2-methylene-3-(3'methyl-2'-oxocyclohexyl)propanoate