ChemicalBook CAS DataBase List 3-OXO-4-PHENYL-BUTYRIC ACID METHYL ESTER

3-OXO-4-PHENYL-BUTYRIC ACID METHYL ESTER synthesis

13synthesis methods

Product Name:3-OXO-4-PHENYL-BUTYRIC ACID METHYL ESTER
CAS Number:37779-49-0
Molecular formula:C11H12O3
Molecular Weight:192.21

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

2033-24-1 Synthesis

2033-24-1
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$6.00/25g

103-80-0
314 suppliers
$13.00/25g

3-OXO-4-PHENYL-BUTYRIC ACID METHYL ESTER

37779-49-0
7 suppliers
$34.82/0.5g

Yield: 72%

Reaction Conditions:

Stage #1:cycl-isopropylidene malonate;phenylacetyl chloride with pyridine in dichloromethane at 0 - 20; for 4.5 h;Inert atmosphere;
Stage #2:methanolReflux;

Steps:

2.1 5.2.1. Methyl 3-oxo-4-phenylbutanoate (7)44
Under N2 atmosphere, pyridine (4 g) was added over 15 min. at0 C to a solution of Meldrum’s acid (6, 2.88 g, 20 mmol) in CH2Cl2(10 mL). A solution of phenylacetyl chloride (5, 3.1 g, 20 mmol) inCH2Cl2 (8 mL) was added dropwise at 0 C during 2 h. After stirringfor 90 min at 0 C and 60 min at rt, CH2Cl2 (5 mL) and 2 M HCl(14 mL) were added. The organic layer was separated and theaqueous layer was extracted with CH2Cl2 (3 10 mL). The organiclayer was dried (Na2SO4) and concentrated in vacuo. The obtainedorange crystals were suspended in methanol (20 mL) and the mixturewas heated to reflux for 3 h. Then the mixture was concentratedin vacuo and the residue was purified by fc (6 cm,cyclohexane/EtOAc = 9:1, 30 mL, Rf = 0.41). Colorless oil, yield2.75 g (72%). C11H12O3 (192.2). MS (EI): m/z = 192 [M], 91 [PhCH2].IR: m [cm1] = 2953 (CAH), 1745 (CO, ester), 1715 (CO, ketone),729, 698 (CAH). 1H NMR (CDCl3): d [ppm] = 3.46 (s, 2H, CH2CO2-CH3), 3.71 (s, 3H, CO2CH3), 3.82 (s, 2H, PhCH2), 7.18-7.38 (m, 5H,arom.).

References:

Knappmann, Inga;Schepmann, Dirk;Wünsch, Bernhard [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 18,p. 4045 - 4055]

103-80-0
314 suppliers
$13.00/25g

37779-49-0
7 suppliers
$34.82/0.5g

References