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ChemicalBook CAS DataBase List Ethyl 1-(hydroxyMethyl)cyclohexanecarboxylate, 97%
834914-39-5

Ethyl 1-(hydroxyMethyl)cyclohexanecarboxylate, 97% synthesis

1synthesis methods
-

Yield:834914-39-5 71%

Reaction Conditions:

with lithium tri-t-butoxyaluminum hydride in tetrahydrofuran;Reflux;

Steps:

24.1 Step 1: Synthesis of ethyl 1-(hydroxymethyl)cyclohexanecarboxylate (24a)

Diethyl cyclohexane-1,1-dicarboxylate (2.12 g, 9.29 mmol) was dissolved in THF (50 mL) and to which was added LiAl(OtBu)3 (5.9 g, 23.2 mmol) in portions. The reaction mixture was stirred at reflux overnight. The reaction was cooled in an ice bath and treated carefully with 10% KHSO4 aq. solution (30 mL) with stirring for 10 min. The precipitate formed was filtered out through a pad of Celite. The filtrate was extracted with EtOAc (3×40 mL) and the organic phase was combined and washed with brine (50 mL), dried over NaSO4, filtered and concentrated in vacuo. The residue was purified with CombiFlash (SiO2) in 0-5% MeOH/ DCM to obtain the desired product ( 24) as an oil (1.23 g, 71% yield). 1H NMR (300 MHz, CDCl3) δ 4.19 (qd, J=7.1, 0.8 Hz, 2H), 3.62 (d, J=6.4 Hz, 2H), 3.46 (s, 1H), 2.00 (dt, J=11.5, 6.4 Hz, 4H), 1.57-1.22 (m, 9H).

References:

US10085999,2018,B1 Location in patent:Page/Page column 123

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