4'-Hydroxyacetophenone → 3,4-Dimethoxy-4'-hydroxychalcone

HRID 1157974Notes

Reaction equation

HRID 1157974 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:16]=O.[OH-].[Na+]>CO>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:1][C:2]([C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=2)=[O:3])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 8419VeratraldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 1813233,4-Dimethoxy-4'-hydroxychalcone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy acetophenone, 1 (13.6 g, 100 mmol), 3,4-dimethoxy benzaldehyde, 5 (16.6 g, 100 mmol) and 50% aqueous sodium hydroxide (80 mL) in methanol (200 mL) were reacted under reflux as in 7 to yield 10. Yield 19.6 g (69%); mp 193-195° C.; MS (FAB) 285 (M++1); IR (KBr) 3443, 1643; 1H NMR (200 MHz, CDCl3) δ 10.45 (s, 1H), 8.10 (d, J=8.5 Hz, 2H), 7.81 (d, J=15.5 Hz, 1H), 7.66 (d, J=15.5 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 6.93 (d, J=8.5 Hz, 2H), 3.95 (s, 3H), 3.92 (s, 3H).

Workup

  1. temperatureunder reflux as in 7

Sources & evidence

ORD record
ord-7a6218d8ab934475a6d7fa0792609dd3
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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