Ethanol → Cinnamoylbenzene

HRID 1019459Notes

Reaction equation

HRID 1019459 reaction equation
O[C:2]1[CH:7]=[C:6](OCOC)[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].CO[C:17]1N=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=1.[OH-].[K+].O.[CH3:28]CO>>[C:20]1([CH:23]=[CH:13][C:12]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)=[O:14])[CH:21]=[CH:28][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 117455591-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone

Product 1

HCID 7189CinnamoylbenzeneYield 34%

Procedure

4.18 g (21.3 mmol) of 1-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone, 2.8 g of 6-methoxy-3-pyridine-carboxaldehyde (20.4 mmol), and 1.8 g (32.1 mmol) of KOH were reacted in 60 ml of EtOH and 20 ml of H2O ml to give 2.18 g (34%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 13.27 (s, 1H), 8.42 (d, J=2.4 Hz, 1H), 7.95-7.82 (m, 3H), 7.50 (d, J=15.6 Hz, 1H), 6.83 (d: J=8.7 Hz, 1H), 6.67 (d, J=2.7 Hz; 1H), 6.61 (d, d, J=2.4, 9.0 Hz, 1H), 5.25 (s, 2H), 4.02 (s, 3H), 3.51 (s, 3H).

Sources & evidence

ORD record
ord-0892f8e6c3e94df4a6055ca6d19263cc
Source dataset
uspto-grants-2014_05
Patent number
US08715761B2

Reaction notes

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