alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 2095972Notes

Reaction equation

HRID 2095972 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].CO[C:13]1[C:18]([CH:19]=O)=[CH:17][CH:16]=[CH:15]N=1.O([CH3:23])[Na]>C1COCC1>[C:18]1([CH:19]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:13]=[CH:23][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 125333912-Methoxypyridine-3-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.39 g (17.6 mmol) of 2-hydroxyacetophenone, 2.10 g of 2-methoxy-3-pyridinecarboxaldehyde (15.3 mmol), and 10 ml of 25% NaOCH3 were reacted in 50 ml of dry THF to give 2.35 g (60%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.85 (s, 1H), 8.24 (d, d, J=1.8, 4.8 Hz, 1H), 8.02 (d, J=15.6 Hz, 1H), 7.94-7.86 (m, 2H), 7.90 (d, J=15.9 Hz, 1H), 7.52 (d, d, J=8.4, 8.7 Hz, 1H), 7.06-6.98 (m, 3H), 4.12 (s, 3H).

Sources & evidence

ORD record
ord-0d10624df89a40c7a206a292d2eee34b
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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