alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 1019451Notes

Reaction equation

HRID 1019451 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][C:12]1[CH:13]=[C:14]([CH:18]=O)O[C:16]=1[CH3:17].O(C)[Na]>C1COCC1>[C:12]1([CH:11]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:13]=[CH:14][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 6434064,5-Dimethyl-2-furaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (14.7 mmol) of 2-hydroxyacetophenone, 1.75 g of 4,5-dimethylfuran-2-carbaldehyde (14.1 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 1.71 g (50%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 13.07 (s, 1H), 7.95 (d, J=7.8 Hz, 1H), 7.61 (d, J=15.0 Hz, 1H), 7.51-7.42 (m, 2H), 7.02 (d, d, J=0.9, 8.4 Hz, 1H), 6.94 (d, d, d, J=1.2, 8.4, 9.0 Hz, 1H), 6.60 (s, 1H), 2.34 (s, 3H), 2.00 (s, 3H).

Sources & evidence

ORD record
ord-3b46b34c96ed4eb88b84f8abeac60810
Source dataset
uspto-grants-2014_05
Patent number
US08715761B2

Reaction notes

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