Potassium Bromide → HCID 70546232, compound

Participants

Reaction Steps

The purified flavanone (833 mg, 2.0 mmol) was hydrogenated over 0.4 g Pd/C at 1 atm for 48 hours as a solution in 85 mL of 10% KOH. Standard workup, followed by recrystallization (H2O--CH3OH), yielded 519 mg (64%) of the substituted dihydrochalcone as light tan needles: mp 227°-228° C. dec; IR (KBr) 3.0-4.4 (OH), 5.80 (carboxylic acid C=O), 5.85 (aliphatic ketone C=O), 6.19 (aromatic ketone C=O) μm; UV (MeOH)λmax 224 nm (ε 22600), 285 (23500); NMR (acetone-d6) 2.84 (t, 2H, J=7 Hz, ArCOCCH2Ar'), 3.37 (t, 2H, J=7 Hz, ArCOCH2CAr'), 3.60 (s, 3H, Ar'OMe), 4.65 (s, 2H, ArOCH2), 6.04 (s, 2H, ArH). Anal. (C20H20O9) C, H. A 189-mg sample of 2,3',6-trihydroxy-4-(2-oxo-3-carboxypropoxy)-4'-methoxydihydrochalcone was titrated to the sodium salt by the general method to yield 200 mg of the sodium salt as a flocculent white solid.

Provenance & Evidence