ChemicalBook CAS DataBase List METHYL 4-ETHYLBENZOATE

METHYL 4-ETHYLBENZOATE synthesis

14synthesis methods

Product Name:METHYL 4-ETHYLBENZOATE
CAS Number:7364-20-7
Molecular formula:C10H12O2
Molecular Weight:164.2

1126-46-1 Synthesis

1126-46-1
228 suppliers
$8.00/25g

925-90-6 Synthesis

925-90-6
345 suppliers
$12.00/5ml

557-20-0
229 suppliers
$14.00/1g

7364-20-7
47 suppliers
$26.00/250mg

Yield: 93%

Reaction Conditions:

Stage #1:ethylmagnesium bromide;diethylzinc in diethyl ether;toluene at -78; for 0.25 h;
Stage #2:Methyl 4-chlorobenzoate;iron-(III)-acetylacetonate in tetrahydrofuran;1-methyl-pyrrolidin-2-one;diethyl ether;toluene at 0;Product distribution / selectivity;

Steps:

8
EXAMPLE 8 Cross Coupling with a Zincate as the Nucleophile A solution of EtMgBr (3 M in Et₂O, 0.9 mL) is added to a solution of Et₂Zn (3 M in toluene, 1 mL) at -78° C. After stirring for 15 min, the resulting cold solution of the zincate is added dropwise to a solution of methyl 4-chlorobenzoate (354 mg, 2.10 mmol) and Fe(acac)₃ (36 mg, 0.1 mmol) in THF (6 mL) and NMP (0.5 mL) at 0° C. causing a spontaneous color change from yellow to brown-black. Standard extractive work up followed by flash chromatography affords 4-ethylbenzoic acid methyl ester (93%) the analytical and spectroscopic data of which are identical to those of a commercial sample.

References:

Furstner, Alois;Leitner, Andreas;Mendez, Maria US2003/220498, 2003, A1 Location in patent:Page/Page column 5; 11

3609-53-8 Synthesis