반응 #164838

반응 방정식

3-Fluorobenzaldehyde

acetone

sodium hydroxide

water

→

yellow crystals

수율 42.0%

1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one

수율 42.0%

용매

ethanol

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 18 hr at room temperature
2. 2
   여과The resulting mixture was filtered
3. 3
   기타chromatographed on silica gel with ethyl acetate/hexane
4. 4
   기타to give a solid
5. 5
   기타The crude was recrystallized from ethanol

실험 절차

3-Fluorobenzaldehyde (1s, 0.5 ml, 4.7 mmol) and acetone (19, 0.18 ml, 2.3 mmol) were combined in ethanol (20 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.29 g, 7.3 mmol) and water (15 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting mixture was filtered and chromatographed on silica gel with ethyl acetate/hexane to give a solid. The crude was recrystallized from ethanol to afford 0.26 g (42%) of yellow crystals: mp 96-97° C. [expected mp 96-97° C.]; 1H NMR: δ 7.03 (d, 2H, J=16.1 Hz), 7.09 (m, 2H), 7.35 (m, 6H), 7.67 (d, 2H, J=15.9 Hz); 13C NMR: δ 114.4, 117.5, 124.4, 126.3, 130.4, 136.9, 142.0, 162.9, 188.1; Anal. Calcd for C17H12OF2: C, 75.55; H, 4.48. Found: C, 75.26; H, 4.65.

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