ChemicalBook CAS DataBase List tert-butyl 2-(4-acetylphenyl)acetate

tert-butyl 2-(4-acetylphenyl)acetate synthesis

5synthesis methods

Product Name:tert-butyl 2-(4-acetylphenyl)acetate
CAS Number:219320-14-6
Molecular formula:C14H18O3
Molecular Weight:234.29

1694-31-1
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13329-40-3 Synthesis

13329-40-3
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219320-14-6
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Yield:219320-14-6 92%

Reaction Conditions:

with 2-Picolinic acid;copper(l) iodide;caesium carbonate in 1,4-dioxane at 70;Inert atmosphere;

Steps:

4 4.3.4 tert-Butyl 2-(4-acetylphenyl)acetate (5d)

General procedure: General procedure for the synthesis of α-arylacetic acid tert-butyl esters: A Schlenk tube was charged with aryl iodide (1.0mmol), CuI (9.5mg, 0.05mmol), 2-picolinic acid (12mg, 0.10mmol), and cesium carbonate (978mg, 3.0mmol). The tube was evacuated and backfilled with argon three times before tert-butyl acetoacetate (2.0mmol) and 2mL of 1,4-dioxane was added. The tube was immersed in an oil bath, and the reaction mixture was stirred at the indicated temperatures for 33-48h. The cooled mixture was partitioned between ethyl acetate and saturated NH₄Cl, the organic layer was washed with brine, dried over Na₂SO₄, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with PE/EA=20:1 to 3:1) to provide the desired α-arylacetic acid tert-butyl esters.

References:

Zhao, Duo;Jiang, Yongwen;Ma, Dawei [Tetrahedron,2014,vol. 70,# 20,p. 3327 - 3332]

5292-43-3 Synthesis