Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)- → HCID 178445649, compound

Participants

Reaction Steps

To a solution of the 4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (862 mg, 5.12 mmol) as obtained above in CH3OH (44 mL) at room temperature was added dropwise sodium methoxide (1.44 mL of 25% by weight, ~4.73M, 6.29 mmol). After stirring for 3 hrs at room temperature, the reaction was quenched by addition of glacial HOAc-ether (1:3) dropwise until the pH was 6-7 followed by addition of a few drops of sat. NaHCO3. The CH3OH was removed under reduced pressure and the residue was partitioned between EtOAc (200 mL deoxygenated by passage of argon) and brine (40 mL). The aqueous layer was extracted with EtOAc (50 mL) and the combined organic extracts were dried (Na2SO4) and concentrated to give crude product (1.6 g). Purification by flash chromatography, eluting with 25% EtOAc/hexane gave trans-4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (690 mg, 4.1 mmol) in 80% yield.

Provenance & Evidence