3-Hydroxy-2,3-diphenylpropanoic acid

Base Information

• Chemical Name: 3-Hydroxy-2,3-diphenylpropanoic acid
• CAS No.: 5449-26-3
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Hs Code.: 2918199090
• European Community (EC) Number: 226-673-2
• NSC Number: 44872,16301
• DSSTox Substance ID: DTXSID60969669
• Nikkaji Number: J210.494F
• Mol file: 5449-26-3.mol

Synonyms:3-hydroxy-2,3-diphenylpropanoic acid;5449-26-3;3-Hydroxy-2,3-diphenylpropionic acid;EINECS 226-673-2;NSC16301;SCHEMBL5178065;DTXSID60969669;NSC44872;NSC 16301;NSC 44872;NSC-16301;NSC-44872;2,3-Diphenyl-3-hydroxypropanoic acid;AC-907/34130032

Chemical Property of 3-Hydroxy-2,3-diphenylpropanoic acid

Chemical Property:

• Vapor Pressure: 4.44E-20mmHg at 25°C
• Refractive Index: 1.626
• Boiling Point: 384.8 °C at 760 mmHg
• Flash Point: 200.7 °C
• PSA: 57.53000
• Density: 1.254 g/cm³
• LogP: 2.58840
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

3-HYDROXY-2,3-DIPHENYLPROPANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Hydroxy-2,3-diphenylpropanoic acid

There total 21 articles about 3-Hydroxy-2,3-diphenylpropanoic 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: 91.0%

2-phenyl-1,1-bis(trimethylsilyloxy)ethene (31491-21-1) + benzaldehyde (100-52-7) → 3-hydroxy-2,3-diphenyl-propionic acid (5449-26-3)

Guidance literature:

With titanium tetrachloride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(01)81183-7

Reference yield: 87.0%

dilithium phenyl acetic acid (15082-44-7,66730-64-1) + benzaldehyde (100-52-7) → α-benzenessigsaeure (4603-32-1,4603-33-2,5449-26-3,52515-81-8,58769-50-9,58769-51-0,93059-95-1)

Guidance literature:

With optically active alkoxide base; In diethyl ether; at -110 ℃; for 0.5h;

DOI:10.1016/0040-4020(84)80003-4

Reference yield:

2-phenyl-1,1-bis(trimethylsilyloxy)ethene (31491-21-1) + benzaldehyde (100-52-7) → (2RS,3RS)-3-hydroxy-2,3-diphenyl-propionic acid (4603-32-1,4603-33-2,5449-26-3,52515-81-8,58769-50-9,58769-51-0,93059-95-1) + α-benzenessigsaeure (4603-32-1,4603-33-2,5449-26-3,52515-81-8,58769-50-9,58769-51-0,93059-95-1)

Guidance literature:

titanium tetrachloride; In dichloromethane; at -50 ℃; for 0.0833333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(01)91225-0

upstream raw materials:

2-bromophenylacetic acid

benzaldehyde

2-phenyl-1,1-bis(trimethylsilyloxy)ethene

phenylacetic acid magnesium enediolate

Downstream raw materials:

(E)-1,2-diphenyl-ethene

(2R,3R)-und (2S,3S)-3-Hydroxy-2,3-diphenylpropansaeure-methylester

cis-stilben

α-benzenessigsaeure-methylester

Refernces

• 1、 Fringuelli, Francesco,Piermatti, Oriana,Pizzo, Ferdinando. "Enantio- and Diastereoselective Aldol-Addition of Chiral Boron Enolates of Carboxylic Acids to Benzaldehyde". . p. 7006 - 7009. Retrieved 2007/10/03.
• 2、 Dubois, Jacqes-Emile,Axiotis, Georges. "KETENE BIS(TRIMETHYLSILYL) ACETALS. CROSS-ALDOL TYPE CONDENSATION REACTIONS WITH ALDEHYDES AND SCHIFF BASES". . p. 2143 - 2146. Retrieved 2007/10/02.