ChemicalBook CAS DataBase List 2,2-Diphenylacetic acid

2,2-Diphenylacetic acid synthesis

13synthesis methods

Product Name:2,2-Diphenylacetic acid
CAS Number:117-34-0
Molecular formula:C14H12O2
Molecular Weight:212.24

298-12-4 Synthesis

298-12-4
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$5.00/25g

71-43-2
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$11.19/25ML

117-34-0
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$6.00/10g

Yield:117-34-0 79%

Reaction Conditions:

with poly(4-vinylpyridine) supported trifluoromethanesulfonic acid at 0 - 20; for 12 h;

Steps:

4.2 General procedure for the condensation reaction of glyoxylic acid with aromatics, using PVP-TfOH(1:10) as the solid acid catalyst
General procedure: The glyoxylic acid, 50 % (0.6 g, 4 mmol), was mixed with arenes (5 mL) in a Nalgene bottle and cooled to 0 °C. Then PVP-TfOH (4.5 g, 28 mmol, 7 equivalents) was added slowly. The reaction mixture was warmed up to room temperature and stirred over specific period of time (Table 1). The reaction progress was monitored by TLC (3:1 hexanes/ethyl acetate). After the reaction was complete, the mixture was poured over ice (25 g), neutralized with sodium bicarbonate, and extracted with diethyl ether (3×15 mL). The organic extracts were combined, washed with water and dried over anhydrous Na₂SO₄. The solvent was removed by vaccum evaporation and crude products were purified by column chromatography on silica gel (70-230 mesh) using hexane/ethyl acetate (85:15) as eluent. The products were characterized by spectral analysis and by comparing the spectral data with those of the authentic samples (in the case of known compounds). Some of the reactions were also repeated in presence of TfOH (7 equivalents, Table 2). Since dichlorobenzene is a solid aromatic compound, it was dissolved in dichloromethane and the solution was used in the reaction.

References:

Prakash, G.K. Surya;Paknia, Farzaneh;Kulkarni, Aditya;Narayanan, Arjun;Wang, Fang;Rasul, Golam;Mathew, Thomas;Olah, George A. [Journal of Fluorine Chemistry,2015,vol. 171,p. 102 - 112]

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