3-OXO-3-P-TOLYL-PROPIONIC ACID ETHYL ESTER synthesis

9synthesis methods

Product Name:3-OXO-3-P-TOLYL-PROPIONIC ACID ETHYL ESTER
CAS Number:27835-00-3
Molecular formula:C12H14O3
Molecular Weight:206.24

122-00-9 Synthesis

122-00-9
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3-OXO-3-P-TOLYL-PROPIONIC ACID ETHYL ESTER

27835-00-3
122 suppliers
$13.00/250mg

Yield: 92%

Reaction Conditions:

Stage #1:para-methylacetophenone;Diethyl carbonate with sodium hydride in tetrahydrofuranReflux;
Stage #2: with acetic acid in tetrahydrofuran

Steps:

5.2. General protocol for synthesis of ethyl 3-aryl-3-oxopropionates (1)
General procedure: To a stirred mixture of sodium hydride (3 mol equiv) washed with hexane (3 × 15 ml), and diethyl carbonate (4 mol equiv) in 50 mL of tetrahydrofuran (THF) was added drop wise appropriately substituted acetophenone (1 mol equiv) over 30 min. Reaction mixture was refluxed for 3-4 h till color changed to dark brown and monitored by TLC (10% ethyl acetate/hexanes). The reaction mixture was cooled and acidified with 5 mL glacial acetic acid followed by addition 100 mL of ice cold dilute HCl solution. The aqueous layer was extracted with ethyl acetate (3 × 75 ml); combined organic phase was washed with saturated sodium bicarbonate, brine and water, dried over anhydrous Na₂SO₄ and evaporated in vacuo, yielded the desired product as viscous mass in excellent yield. The compounds were characterized on the basis of their ¹H NMR and ¹³C NMR spectra as reported in the literature.

References:

Kumar, Satish;Namkung, Wan;Verkman;Sharma, Pawan K. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 14,p. 4237 - 4244] Location in patent:experimental part