ChemicalBook CAS DataBase List Triethyl 1,3,5-benzenetricarboxylate

Triethyl 1,3,5-benzenetricarboxylate synthesis

8synthesis methods

Product Name:Triethyl 1,3,5-benzenetricarboxylate
CAS Number:4105-92-4
Molecular formula:C15H18O6
Molecular Weight:294.3

623-47-2
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4105-92-4
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$32.20/5g

1,2,4-Benzenetris(carboxylic acid ethyl) ester

14230-18-3
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Yield: 92%

Reaction Conditions:

with bis(1,5-cyclooctadiene)nickel⁽⁰⁾;triphenylphosphine in toluene at 23; for 2 h;Inert atmosphere;

Steps:

2 Example 2 Catalytic [2+2+2] Cyclotrimerization of Ethyl Propiolate
Under an argon atmosphere, Ni(COD)₂ (5.5 mg, 0.020 mmol; Acros, Pittsburgh, Pa.; catalog No. 223970050) and PPh₃ (15.6 mg, 0.060 mmol; Sigma-Aldrich Co., St. Louis, Mo.; catalog No. T84409) were mixed in 10 mL of toluene at 23° C.
The resulting mixture was stirred at this temperature for 5 min to produce a stock solution of the catalyst.
A portion of the stock solution (375 μL) was added to a 10 mL scintillation vial under an argon atmosphere and the volume was brought to 2 mL with toluene, followed by the addition of ethyl propiolate (152 μL, 1.5 mmol).
The reaction was complete within 2 h, producing a mixture of 1,2,4- and 1,3,5-isomers in a 97:3 molar ratio.
The 1,2,4-isomer (triethyl trimellitate) was separated from the isomeric mixture using column chromatography (eluted with diethyl ether/hexanes) and isolated in 92% yield. ¹H NMR (400 MHz, CDCl₃, δ): 8.41 (1H, d, ⁴J_H-H=1.7 Hz, ArH), 8.20 (1H, dd, ³J_H-H=7.9 Hz, ⁴J_H-H=1.7 Hz, ArH), 7.76 (1H, d, ³J_H-H=7.9 Hz, ArH), 4.50-4.35 (6H, m, CH₂), 1.50-1.35 (9H, m, CH₃); ¹³C{¹H} NMR (101 MHz, CDCl₃, δ): 167.24, 166.70, 165.07, 136.36, 132.77, 132.17, 132.10, 130.19, 128.95, 62.09, 62.03, 61.78, 14.36, 14.20, 14.15.