Hydrochloric Acid → HCID 56653338, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-sec-butyl-4-hydroxyisophthalaldehyde of formula I (0.50 g, 3.05 mmol) and p-methyl acetophenone (0.41 g, 3.05 mmol) in dioxane (25 mL) was treated with conc.HCl (0.5 mL). The solution was heated at 80° C. for 2.5 h. Further, 0.5 mL of conc.HCl was added and reaction was continued for 2.5 h more. Most of the excess reagent was evaporated under reduced pressure, and the residue was suspended in water (50 mL) and extracted 3-fold with CHCl3 (50 mL). The combined organic layers were dried on Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel (SiO2, 230-400 flash), eluting with a gradient of 4% ethyl acetate in hexane, which upon concentration provides (E)-3-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde (General Formula III).

Provenance & Evidence