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

Propanoic acid, 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-, phenylmethyl ester

1159999-13-9

42017-89-0

General procedure for the synthesis of fenofibric acid from compound (CAS:1159999-13-9): to a solution of compound 104 (5.00 g, 12.2 mmol) in ethanol (150 mL) was added a solution of potassium hydroxide (2.74 g, 48.9 mmol) in ethanol (50 mL). The reaction mixture was heated to reflux and stirred for 16 hours. Upon completion of the reaction, ethanol was removed under vacuum and water (200 mL) was added to the residue. The aqueous solution was washed with ether (2 x 100 mL) to remove nonpolar impurities, followed by acidification of the aqueous solution with 2N HCl to pH 1. The acidified aqueous solution was extracted with ethyl acetate (2 x 150 mL), the organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give compound 105 (3.57 g, 91% yield) as an off-white solid . The product was characterized by 1H NMR (300 MHz, CD3OD): δ 7.75-7.70 (m, 4H), 7.52 (d, J = 8.6 Hz, 2H), 6.96 (d, J = 9.0 Hz, 2H), 1.65 (s, 6H).

67-66-3 Synthesis

67-66-3
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42019-78-3 Synthesis

42019-78-3
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$24.00/10g

67-64-1
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42017-89-0
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$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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1159999-13-9
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42017-89-0
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References