Sodium Hydroxide → 1-(2-Hydroxyphenyl)-3-(4-methoxyphenyl-2-propen-1-one

HRID 1157973Notes

Reaction equation

HRID 1157973 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-:21].[Na+].[K+].[Br-]>CO>[OH:21][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH:2]=[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 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 68490alpha-HydroxyacetophenoneHCID 253877Potassium Bromide

Product 1

HCID 955471-(2-Hydroxyphenyl)-3-(4-methoxyphenyl-2-propen-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxy acetophenone, 3 (6 mL, 50 mmol), 4-methoxy benzaldehyde, 4 (6 mL, 50 mmol) and 50% aqueous sodium hydroxide (50 mL) in methanol (100 mL) were reacted as in 7 to yield 9. Yield 11.7 g (92%); mp 81-83° C. (lit. 93-94);227 MS (FAB) 255 (M++1); IR (KBr) 3450, 1639; 1H NMR (200 MHz, CDCl3) δ 7.92 (dd, J=8.7 Hz, 1.4 Hz, 1H), 7.90 (d, J=15.4 Hz, 1H), 7.62 (d, J=8.7 Hz, 2H), 7.53 (d, J=15.5 Hz, 1H), 7.49 (t, J=7.4 Hz, 1H), 6.95 (d, J=8.6 Hz, 2H), 7.03-6.89 (m, 2H), 3.86 (s, 3H).

Workup

  1. customto yield 9

Sources & evidence

ORD record
ord-b7e6764485574e2f955f75549bf682d2
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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