Potassium Bromide → HCID 70546232, compound

HRID 1702581Notes

Reaction equation

[K+].[Br-].[OH:3][CH:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12](=[O:17])[CH2:13][C:14]([OH:16])=[O:15])[CH:7]=[C:6]([OH:18])[CH:5]1[CH:19]=[CH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([OH:31])[CH:24]=1)=[O:22].[Na:32]>>[Na:32].[OH:18][CH:6]1[CH:7]=[C:8]([O:10][CH2:11][C:12](=[O:17])[CH2:13][C:14]([OH:16])=[O:15])[CH:9]=[C:4]([OH:3])[CH:5]1[CH:19]=[CH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([OH:31])[CH:24]=1)=[O:22]

Participants

Reactant 3

HCID 253877Potassium Bromide

HCID 5360545Sodium

HCID 70546233HCID 70546233, compound

Product 1

HCID 70546232HCID 70546232, compound

Procedure

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.

Sources & evidence

ORD record: ord-c24ec6356e1d48dfb0bbe86d4423daa2
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04348333

Reaction notes

Loading…