2-Methyl-3,3-diphenylprop-2-enoic acid

Base Information

• Chemical Name: 2-Methyl-3,3-diphenylprop-2-enoic acid
• CAS No.: 17684-12-7
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• NSC Number: 159013
• DSSTox Substance ID: DTXSID20303545
• Nikkaji Number: J1.616.799A
• Mol file: 17684-12-7.mol

Synonyms:17684-12-7;2-methyl-3,3-diphenylacrylic acid;2-methyl-3,3-diphenylprop-2-enoic acid;NSC159013;SCHEMBL585335;DTXSID20303545;AKOS004905762;NSC-159013

Chemical Property of 2-Methyl-3,3-diphenylprop-2-enoic acid

Chemical Property:

• Vapor Pressure: 1.65E-05mmHg at 25°C
• Boiling Point: 350.3°Cat760mmHg
• Flash Point: 252.4°C
• Density: 1.146g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 298

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C(C1=CC=CC=C1)C2=CC=CC=C2)C(=O)O

Technology Process of 2-Methyl-3,3-diphenylprop-2-enoic acid

There total 21 articles about 2-Methyl-3,3-diphenylprop-2-enoic 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: 99.0%

benzophenone (119-61-9) + ethyl 2,2-dibromopropanoate (34757-17-0) → 2-methyl-3,3-diphenyl-2-propenoic acid (17684-12-7)

Guidance literature:

ethyl 2,2-dibromopropanoate; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 20 ℃;

benzophenone; In tetrahydrofuran; pentane; at 20 ℃; for 0.5h;

DOI:10.1021/jo0497813

Reference yield: 97.0%

benzophenone (119-61-9) + (2,6-di-t-butyl)-phenyl propanoate (40662-79-1) → 2-methyl-3,3-diphenyl-2-propenoic acid (17684-12-7)

Guidance literature:

(2,6-di-t-butyl)-phenyl propanoate; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 0 ℃; for 2.5h; Inert atmosphere;

With ethylene dibromide; In tetrahydrofuran; pentane; at 0 ℃; for 0.5h; Inert atmosphere;

benzophenone; In tetrahydrofuran; pentane; at 0 - 20 ℃; for 0.166667h; Reagent/catalyst; Temperature; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02069

Reference yield: 81.0%

iodobenzene (591-50-4) + (Z)-2-methyl-3-phenyl-3-(triethylgermyl)propenoic acid (940964-87-4) → 2-methyl-3,3-diphenyl-2-propenoic acid (17684-12-7)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 80 ℃; for 2h; Molecular sieve;

DOI:10.1002/adsc.201100627

upstream raw materials:

2-methyl-3,3-diphenyl-acrylic acid ethyl ester

sulfuric acid

ethyl 3-hydroxy-2-methyl-3,3-diphenylpropionate

acetic acid

Downstream raw materials:

2-methyl-3-phenylinden-1-one

α-methyl-β,β-diphenylpropionic acid

Refernces

• 1、 Sun, Jun,Yoshiiwa, Toshiya,Iwata, Takayuki,Shindo, Mitsuru. "Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters". . p. 6585 - 6588. Retrieved 2019/09/30.
• 2、 Umezu, Satoshi,Yoshiiwa, Toshiya,Tokeshi, Manabu,Shindo, Mitsuru. "Generation of ynolates via reductive lithiation using flow microreactors". . p. 1822 - 1825. Retrieved 2014/03/21.