ChemicalBook CAS DataBase List METHYL 4-VINYLBENZOATE

METHYL 4-VINYLBENZOATE synthesis

11synthesis methods

Product Name:METHYL 4-VINYLBENZOATE
CAS Number:1076-96-6
Molecular formula:C10H10O2
Molecular Weight:162.19

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

1075-49-6 Synthesis

1075-49-6
299 suppliers
$17.00/1g

1076-96-6
125 suppliers
$31.00/250mg

Yield:1076-96-6 90%

Reaction Conditions:

with bromobenzene at 55 - 60; under 3750.38 - 4500.45 Torr; for 6 h;Autoclave;

Steps:

General procedure for the esterification
General procedure: benzoic acid (Table 3, entry 1) (1.0 g,0.0081 mol), bromobenzene (0.125 g, 0.0081 mol), 10% palladium on carbon(50% wet) (0.2 g) and methanol (3 mL) were placed in autoclave vessel. Autoclave was pressurized with 1-2 bar of nitrogen followed by 1-2 bar of hydrogen gas and then put under the desired pressure of hydrogen (5-6 bar).The reaction mixtures are then warmed to 55-60 C temperature and stirredfor 4 h at 300 rpm. After reaction, the catalyst was filtered through celite bed.Filtrate was added with water (30 mL). The reaction mixture was extracted with isopropyl acetate (2 15 mL). The combined organic layers were washedwith 5% aqueous sodium bicarbonate solution (2 15 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum togive of methyl benzoate product (Table 3, entry 7): Colorless oil;¹H NMR (400 MHz, CDCl₃):d = 7.93-7.92 (dd, J = 7.5 Hz, 2 H),7.26-7.24 (dd, J = 7.5 Hz, 2 H), 3.83 (s, 3 H), 2.62 (m, 2H), 1.25 (t,3H). ¹³C NMR (100 MHz, CDCl₃): δ 15.2, 28.9, 51.8, 127l.7, 127.9, 129.7, 149.7,167.1

References:

Aavula, Sanjeev Kumar;Chikkulapalli, Anil;Hanumanthappa;Jyothi, Indira;Vinod Kumar;Manjunatha, Sulur G. [Tetrahedron Letters,2013,vol. 54,# 42,p. 5690 - 5694]

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