Sulfuric Acid → HCID 59378156, compound

Participants

Reaction Steps

4-(5-Oxo-5-phenyl-penta-1,3-dienyl)-benzoic acid (13.9 g, 50 mmol) is dissolved in ethanol (280 mL). Concentrated H2SO4 (1 mL) and 5% palladium on carbon (2.8 g) are added and the mixture hydrogenated at 50° C. and 60 psi for 4 h. The reaction is filtered, diluted with water (1000 mL), and extracted several times with diethyl ether. The combined organic extracts are washed with 2 N NaOH. The aqueous portion is acidified with concentrated hydrochloric acid and extracted with diethyl ether. The ether extracts are washed with water, dried over Na2SO4, and evaporated to obtain a solid. The solid is recrystallized from hexanes to obtain 7.2 g (54%) of white crystals. m.p.=80-80.5° C.; Anal. Calcd for C18H20O2: C, 80.56; H, 7.51. Found: C, 80.75; H, 7.34.

Provenance & Evidence