Morpholine → Ethyl 2,6-dimethyl-3-(propan-2-yl)benzoate

Participants

Reaction Steps

Morpholine (13.34 g), isovaleraldehyde (13.18 g), p-toluenesulfonic acid (0.2 g), and toluene (300 ml) were combined and heated at reflux using a Soxhlet extractor with magnesium sulfate to remove any water produced. After three hours the Soxhlet extractor was replaced with a condenser, and ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (30 g) was added. The reaction mixture was heated under reflux for approximately 64 hours. The solvent was evaporated, and the resultant oil was distilled to give 11.1 g of crude product which was chromatographed to yield ethyl 2,6-dimethyl-3-(1-methylethyl)benzoate (2.8 g).

Provenance & Evidence