Réaction #73279

Équation de réaction

Ethyl 4-oxocyclohexanecarboxylate

lithium tetrahydroaluminate

→

4-(Hydroxymethyl)cyclohexanol

Solvants

ether

ether

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was quenched with water (2 mL) and 1 N NaOH (2 mL) and ether
2. 2
   workup.ADDITIONwas added (100 mL)
3. 3
   FiltrationThe precipitated solids were filtered off
4. 4
   Autrethe residue was used in the next reaction

Mode opératoire

Ethyl 4-oxocyclohexanecarboxylate (2.0 g, 0.012 mol) was dissolved in ether (20.0 mL) and was then cooled at 0° C. Into the mixture was added 1 M lithium tetrahydroaluminate in ether (20 mL) and the resulting mixture was stirred at 0° C. for 2 hours. The reaction was quenched with water (2 mL) and 1 N NaOH (2 mL) and ether was added (100 mL). The precipitated solids were filtered off and the residue was used in the next reaction. 1H NMR(CDCl3): δ 4.02 and 3.75 (m, 1H), 3.45-3.61 (m, 2H), 2.02 (m, 2H), 1.84 (m, 1H), 1.52-1.80 (m, 2H), 1.44 (m, 1H), 1.32 (m, 2H), 1.03 (m, 1H).

Source