alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 1019443Notes

Reaction equation

HRID 1019443 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]1N=[C:17]([CH:19]=O)[CH:16]=[CH:15][CH:14]=1.O([CH3:23])[Na]>C1COCC1>[C:13]1([CH:23]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:19]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 123253926-Methoxy-2-pyridinecarboxaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.35 g (17.3 mmol) of 2-hydroxyacetophenone, 2.13 g of 6-methoxy-2-pyridinecarboxaldehyde (15.5 mmol), and 8 ml of 25% NaOCH3 were reacted in 70 ml dry THF to give 1.2 g (30%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.15 (s, 1H), 8.24 (d, J=14.7 Hz, 1H), 8.01 (d, d, J=1.2, 7.8 Hz, 1H), 7.79 (d, J=15.0 Hz, 1H), 7.65 (d, d, J=7.2, 7.2 Hz, 1H), 7.53 (d, d, J=7.2, 7.2 Hz, 1H), 7.10 (d, J=7.2 Hz, 1H), 7.06 (d, d, J=0.9, 8.1 Hz, 1H), 6.99 (d, d, J=7.2, 8.1 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 4.08 (s, 3H).

Sources & evidence

ORD record
ord-cb479625b5a748da96aa65b3c7c528b4
Source dataset
uspto-grants-2014_05
Patent number
US08715761B2

Reaction notes

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