ChemicalBook CAS DataBase List Ethyl 4-oxocyclohexanecarboxylate

Ethyl 4-oxocyclohexanecarboxylate synthesis

9synthesis methods

Product Name:Ethyl 4-oxocyclohexanecarboxylate
CAS Number:17159-79-4
Molecular formula:C9H14O3
Molecular Weight:170.21

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64-17-5 Synthesis

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Yield:17159-79-4 84%

Reaction Conditions:

with thionyl chloride in neat (no solvent) at 0 - 25; for 3 h;

Steps:

9 Synthesis of ethyl 4-oxocyclohexane-1-carboxylate (1):

To a solution of 4-oxocyclohexane-1-carboxylic acid (SM-1) (1 g, 6.41 mmol) in ethanol (10 mL) was added thionyl chloride (0.56 mL, 7.69 mmol) drop wise at 0 °C; warmed to RT and stirred for 3 h. After consumption of the starting material (by TLC), volatiles were evaporated under reduced pressure. Obtained crude material was dissolved in EtOAc (20 mL) and washed with aqueous NaHCO₃ solution. Organic layer was dried over Na₂SO₄ and concentrated to obtain compound 1 (1 g, 84 %) as brown liquid. (0427) 1H NMR (500 MHz, CDCl₃): δ 4.16 (q, J = 7.0 Hz, 2H), 2.77-2.70 (m, 1H), 2.50-2.43 (m, 2H), 2.38-2.30 (m, 2H), 2.23-2.16 (m, 2H), 2.05-1.95 (m, 2H), 1.26 (t, J = 7.1 Hz, 3H). LCMS (m/z): 171.3 [M⁺+1]

References:

WO2018/26763,2018,A1 Location in patent:Page/Page column 6