ChemicalBook CAS DataBase List ETHYL 4-TERT-BUTYLBENZOYLFORMATE

ETHYL 4-TERT-BUTYLBENZOYLFORMATE synthesis

7synthesis methods

Product Name:ETHYL 4-TERT-BUTYLBENZOYLFORMATE
CAS Number:80120-36-1
Molecular formula:C14H18O3
Molecular Weight:234.29

29786-93-4 Synthesis

29786-93-4
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3972-65-4 Synthesis

3972-65-4
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$8.00/10g

95-92-1 Synthesis

95-92-1
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$5.00/5G

80120-36-1
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$68.00/5g

Yield:80120-36-1 29%

Reaction Conditions:

Stage #1: n-butyllithium;1-bromo-4-tert-butylbenzene in tetrahydrofuran;hexanes at -78; for 1 h;
Stage #2: oxalic acid diethyl ester in tetrahydrofuran;hexanes at -78; for 1 h;

Steps:

26.a

To a solution of 4-bmmo-tert- butylbenzene (0.70 mL, 5.0 mmol) in THF (20 mL) was dropwise added n-BuLi (2.87 M solution in Hexanes, 1.74 mL, 5.0 mmol) at -78° C under a nitrogen atmosphere. After stirring for 1 h diethyl oxylate (0.68 mL, 5.0 mmol) was added. The reaction stirred for 1 h at -78° C and then 1 N HCl was added. The solution was diluted with H₂O and EtOAc and the layers separated. The aqueous phase was backextracted with EtOAc several times. The combined organic layers were washed with Brine, dried (MgSO₄), filtered and concentrated. The product was purified by column chromatography (SiO₂, 5-10% EtOAc/Hexanes) to give the title compound (334 mg, 29%). IH NMR (400 MHz, CHLOROFORM- d) δ ppm 7.97 (dt, J=8.65, 2.12 Hz, 2 H) 7.55 (dt, J=8.84, 2.02 Hz, 2 H) 4.47 (q, J=7.07 Hz, 2 H) 1.45 (t, J=7.20 Hz, 3 H) 1.37 (s, 9 H).

References:

WO2008/89052,2008,A2 Location in patent:Page/Page column 42

253185-04-5 Synthesis