Ketene → HCID 178425354, compound

Participants

Reaction Steps

4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexane-carbaldehyde (20.6 g, 72 mmol, ratio of trans-4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexanecarbaldehyde/cis-4-(trans-4-(4-methylphenyl)cyclohexyl)-cyclohexylcarbaldehyde=98/2) was dissolved in ethyl acetate (380 g), and iron chloride (FeCl3, 0.2 g, 1.2 mmol) was added thereto. 3.7 equivalents of ketene was introduced into the solution at 40° C. over 150 minutes. After completing the introduction of ketene, nitrogen was introduced for 30 minutes to eliminate the unreacted ketene. The resulting solution was concentrated to provide 4-(4-(trans-4-(4-methylphenyl)-cyclohexyl)cyclohexyl)-2-oxetanone (ratio of 4-(trans-4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexyl)-2-ox etanone/4-(cis-4-(trans-4-(4-methylphenyl)cyclohexyl)-cyclohexyl)-2-oxetanone=98/2) (27.8 g, 64 mmol, yield: 88%)).

Provenance & Evidence