ChemicalBook CAS DataBase List Cyclohexanecarboxylic acid, 4-oxo-, phenylmethyl ester

Cyclohexanecarboxylic acid, 4-oxo-, phenylmethyl ester synthesis

7synthesis methods

Product Name:Cyclohexanecarboxylic acid, 4-oxo-, phenylmethyl ester
CAS Number:62596-26-3
Molecular formula:C14H16O3
Molecular Weight:232.27

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Cyclohexanecarboxylic acid, 4-oxo-, phenylmethyl ester

62596-26-3
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Yield:62596-26-3 92%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 48 h;

Steps:

I Intermediate AA48: Benzyl 4-oxocyclohexanecarboxylate

To a solution of 4-oxocyclohexanecarboxylic acid AA47 (20.0 g, 0.141 mol) , potassium carbonate (38.9 g, 0.282 mol) in N, N-dimethylformamide (100 mL) was added (bromomethyl) benzene (28.8 g, 0.169 mol) . The mixture was stirred at room temperature for 2 days. The reaction mixture was poured into water (450 mL) and extracted with ethyl acetate (200 mL) for three times. The combined organic layers were washed with water (100 mL) , brine (100 mL) , dried over Na₂SO_{4 (s)}, filtered and concentrated to give the crude product, which was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 10 : 1 to 5 : 1) to give the title compound (30.0 g, 92 %yield) as yellow oil.¹H NMR (300 MHz, DMSO-d₆) δ 7.37 -7.26 (m, 5H) , 5.12 -5.05 (m, 2H) , 2.91 -2.79 (m, 1H) , 2.41 -2.31 (m, 2H) , 2.23 -2.08 (m, 4H) , 1.87 -1.72 (m, 2H) .

References:

WO2019/214610,2019,A1 Location in patent:Page/Page column 63