3-Hydroxyacetophenone → 3'-Hydroxy-4-methoxy-chalcone

HRID 1157972Notes

Reaction equation

HRID 1157972 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[Na+].[K+].[Br-]>CO>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:2](=[O:3])[CH:1]=[CH:17][C:16]1[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 84873-HydroxyacetophenoneHCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 253877Potassium Bromide

Product 1

HCID 686436623'-Hydroxy-4-methoxy-chalcone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxy acetophenone, 2 (6.8 g, 50 mmol), 4-methoxy benzaldehyde, 4 (6.0 mL, 50 mmol) and 50% aqueous sodium hydroxide (50 mL) in methanol (110 mL) were reacted as in 7 to yield 8. Yield 12.5 g (98%); mp 93-94° C.; MS (FAB) 255 (M++1); IR (KBr) 3366, 1649; 1H NMR (200 MHz, CDCl3) δ 7.80 (d, J=15.6 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.58 (d, J=8.7 Hz, 2H), 7.55 (d, J=2.3 Hz, 1H), 7.38 (d, J=15.6 Hz, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.04 (d, J=7.9 Hz, 1H), 6.92 (d, J=8.6 Hz, 2H), 3.85 (s, 3H).

Workup

  1. customto yield 8

Sources & evidence

ORD record
ord-5286dd400e364e45b006f3c82a0bc050
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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