ChemicalBook CAS DataBase List AKOS 91083

AKOS 91083 synthesis

4synthesis methods

Product Name:AKOS 91083
CAS Number:79669-11-7
Molecular formula:C12H16O3
Molecular Weight:208.25

586960-22-7 Synthesis

586960-22-7
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$90.00/500mg

79669-11-7
13 suppliers
$140.00/500mg

Yield:-

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol;ethyl acetate; under 4121.6 Torr; for 16 h;

Steps:

10

A 125 mL Ehrlenmayer flask equipped with a magnetic stirrer bar was charged with 7.76 g (47.8 mmol) of 4-Isopropoxybenzaldehyde, 5.28 g (50.7 mmol) of malonic acid and 2.2 mL (2.2g, 27.2 mmol) of pyridine. The slurry was heated to 80⁰C, at which temperature a clear yellow solution formed. After stirring for 2 hr, the reaction mixture was cooled to 25°C. The resulting solid was isolated by filtration, rinsing with water (2 X 30 mL) and 2: 1 methyl t-butyl ether (MTBE)/hexanes (2 X 30 mL). A total of 3.1 g of 4-Isopropoxycinnamic acid was isolated. A 500 mL Parr shaker reaction vessel was charged with 3.10 g (15.2 mmol) of 4-t- butylcinnamic acid, 20 mL of ethyl acetate and 10 mL of ethanol. This mixture was treated with 0.15 g of 10% palladium on charcoal and placed under an atmosphere of 51 psig of hydrogen gas in a Parr shaker apparatus. A total of 14 psig of hydrogen was taken up in 16 hours. The reaction mixture was removed from the Parr shaker apparatus after dissipating the hydrogen gas, filtered through a Celite pad to remove the catalyst and concentrated to a white solid, 3-(4-4-Isopropoxyphenyl)propanoic acid (3.07 g). IH NMR (d6-DMSO): δ 12.0, bs, IH (COOH); δ 7.00, d, 2H, (arylH's meta to O); δ 6.70, d, 2H (arylH's ortho to O); δ 4.43, hept, IH, (OCH); δ 2.63, t, 2H, (CH₂ α to aryl); δ 2.38, t, 2H (CH₂ α to COOH); δ 1.13, d, 6H (CH₃'s). ¹³C NMR (d6-DMS0): 173.78, 155.69, 132.50, 129.18, 115.44, 68.98, 35.50, 29.47, 21.85.

References:

WO2008/112368,2008,A2 Location in patent:Page/Page column 32-33