alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 2095978Notes

Reaction equation

HRID 2095978 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].O1CCN([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)CC1.O(C)[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:23]=[CH:24][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 2913494-MorpholinobenzaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.15 g (15.8 mmol) of 2-hydroxyacetophenone, 2.8 g of 4-morpholinobenzaldehyde (14.5 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 2.52 g (56%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.99 (s, 1H), 8.43 (d, J=2.4 Hz, 1H), 7.93-7.84 (m, 3H), 7.52-7.48 (m, 2H), 7.03 (d, d, J=0.9, 8.4 Hz, 1H), 6.97-6.92 (m, 1H), 6.68 (d, J=9.0 Hz, 1H), 3.86-3.83 (m, 4H), 3.69-3.66 (m, 4H).

Sources & evidence

ORD record
ord-3d34b574710b4d48aebe7f49add191d3
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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