alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 2095984Notes

Reaction equation

HRID 2095984 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19]N=2)CCCCC1.O([CH3:27])[Na]>C1COCC1>[C:20]1([CH:21]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:19]=[CH:27][CH:17]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 27639806-(Piperidin-1-yl)pyridine-3-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.72 g (12.6 mmol) of 2-hydroxyacetophenone, 2.0 g of 6-(piperidin-1-yl)nicotinaldehyde (10.5 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 1.41 g (43.5%) of chalcone after purification. 1H NMR (300 Hz, CDCl3): δ 13.10 (s, 1H), 8.39 (d, J=2.4 Hz, 1H), 7.93-7.89 (m, 2H), 7.80 (d, d, J=2.4, 9.0 Hz), 7.51-7.42 (m, 2H), 7.03 (d, d, J=0.9, 8.4 Hz, 1H), 6.94 (d, d, d, J=1.2, 7.2, 8.1 Hz, 1H), 6.68 (d, J=9.0 Hz, 1H), 3.71-3.67 (m, 4H), 1.75-1.67 (m, 6H).

Sources & evidence

ORD record
ord-19d1b4acce7f439c9523f6238c175f83
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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