ChemicalBook CAS DataBase List Fenofibric acid

Fenofibric acid synthesis

8synthesis methods

Product Name:Fenofibric acid
CAS Number:42017-89-0
Molecular formula:C17H15ClO4
Molecular Weight:318.75

67-66-3 Synthesis

67-66-3
6 suppliers
$33.60/500ml

42019-78-3 Synthesis

42019-78-3
507 suppliers
$24.00/10g

67-64-1
6 suppliers
$17.30/10ml

42017-89-0
397 suppliers
$5.00/100mg

Yield:42017-89-0 73%

Reaction Conditions:

Stage #1:4-chloro-4'-hydroxybenzophenone;acetone with sodium hydroxide for 2 h;Heating / reflux;
Stage #2:chloroform in acetone for 8 h;Heating / reflux;

Steps:

VII.1
A mixture of 4-chloro-4'-hydroxybezophenone (116 g, 0.500 mole) and sodium hydroxide (120 g, 3.00 mole) in acetone (1 L) was heated to reflux for 2 hours. The heating was stopped and the heating source was removed. A mixture of chloroform (179 g, 1.50 mole) in acetone (300 mL) was added drop-wise. The reaction mixture was stirred overnight without heating. The mixture was heated to reflux for 8 hours and then allowed to cool to room temperature. The precipitate was removed by filtration and washed with acetone (100 mL). The filtrate was concentrated under reduced pressure to give a brown oil. Water (200 mL) was added to the brown oil and was acidified (to pH=l) with IN hydrochloric acid. The precipitate, which formed was filtered and dried under high vacuum. The remaining yellow solid (268 g) was recrystallized from toluene in 4 batches (400 mL toluene each). After filtration and drying under high vacuum, the experiment produced fenofibric acid (116 g, 73% yield) as a light yellow solid. 'H NMR (300 MHz, DMSO-d6): 6 = 13.22 (1H, s, br), 7.72 (4H, d, J= 8.4 Hz), 7.61 (2H, d, J= 7. 8 Hz), 6.93 (2H, d, J= 7. 8 Hz), 1.60 (6H, s). "C NMR (75 MHz, DMSO-d6) : 5 = 192.96, 174.18, 159.35, 136.84, 136.12, 131.67, 131.02, 129.12, 128. 43, 116. 91,78. 87,25. 13.

References:

SIGNATURE PHARMACEUTICALS, LLC WO2005/46575, 2005, A2 Location in patent:Page/Page column 176-177

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