alpha-Hydroxyacetophenone → Cinnamoylbenzene

HRID 2095985Notes

Reaction equation

HRID 2095985 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.S1C=CN=[C:12]1[CH:16]=O.[O:18]([CH3:20])[Na]>C1COCC1>[C:5]1([CH:3]=[CH:2][C:20]([C:16]2[CH:12]=[CH:6][CH:5]=[CH:3][CH:2]=2)=[O:18])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 27349031,3-Thiazole-2-carbaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.29 g (16.8 mmol) of 2-hydroxyacetophenone, 1.8 g of thiazole-2-carbaldehyde (15.9 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 0.254 g (27%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.62 (s, 1H), 8.08-7.94 (m, 4H), 7.57-7.51 (m, 2H), 7.06 (d, d, J=1.2, 8.4 Hz, 1H), 6.98 (d, d, d, J=1.2, 7.2, 8.1 Hz, 1H).

Sources & evidence

ORD record
ord-9fcf0ea61aee4fd2af2d721ecc79470b
Source dataset
uspto-grants-2013_05
Patent number
US08449936B2

Reaction notes

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