alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 2095986Notes

Reaction equation

HRID 2095986 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].Cl[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14]N=1.O([CH3:22])[Na]>C1COCC1>[C:15]1([CH:16]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:18]=[CH:19][CH:12]=[CH:22][CH:14]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 27640536-Chloropyridine-3-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.08 g (15.3 mmol) of 2-hydroxyacetophenone, 2.05 g of 6-chloronicotinaldehyde (14.5 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 0.55 g (15%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.61 (s, 1H), 8.66 (d, J=2.4 Hz, 1H), 7.97-7.92 (m, 2H), 7.90 (D, J=15.9 Hz, 1H), 7.71 (d, J=15.6 Hz, 1H), 7.55 (d, d, d, J=1.5, 7.2, 8.7 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 7.06 (d, d, J=0.9, 8.4 Hz, 1H), 6.98 (d, d, d, J=1.2, 7.5, 8.1 Hz, 1H).

Sources & evidence

ORD record
ord-25121b1e82a74c51bc84a840ca97564c
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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