ChemicalBook CAS DataBase List ETHYL CYCLOHEXYL PROPIONATE

ETHYL CYCLOHEXYL PROPIONATE synthesis

10synthesis methods

Product Name:ETHYL CYCLOHEXYL PROPIONATE
CAS Number:2511-00-4
Molecular formula:C11H20O2
Molecular Weight:184.28

Ethyl cyclohexane propionate is produced by esterification of Ethyl cyclohexanol with Propionic acid or Propionic anhydride.

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Yield:2511-00-4 95%

Reaction Conditions:

Stage #1: ethyl 2-cyclohexylacetatewith lithium hexamethyldisilazane in tetrahydrofuran at -78; for 1 h;
Stage #2: methyl iodine in tetrahydrofuran at -78 - 20; for 18 h;

Steps:

3.8c Ethyl 2-cyclohexylpropanoate

LiHMDS (1M in THF; 58 mL; 58 mmol) was added drop wise to a stirred solution of ethyl 2-cyclohexylacetate (9 mL; 50 mmol) in anhydrous THF (20 mL), at -78° C. The mixture was stirred at -78° C. for 1 h then MeI (3.75 mL; 60.0 mmol) was added. The mixture was allowed to gradually warm to room temperature, stirred an additional 18 h, then quenched with H₂O (100 mL) and extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine, dried over MgSO₄and concentrated. The residue was purified on silica gel using Hexane/EtOAc gradient to obtain ethyl 2-cyclohexylpropanoate as a colorless oil (8.75 g, 95%). ¹H NMR (DMSO-d₆) δ: 0.83-1.00 (m, 2H), 1.01 (d, J=7.0 Hz, 3H), 1.05-1.25 (m, 2H), 1.17 (t, J=7.1 Hz, 3H), 1.40-1.51 (m, 1H), 1.51-1.74 (m, 6H), 2.19 (pseudo p, J=7.1 Hz, 1H), 3.97-4.11 (m, 2H). MS 185 (MH⁺).

References:

US2015/376136,2015,A1 Location in patent:Paragraph 0894