Furfural → Cinnamoylbenzene

HRID 1019449Notes

Reaction equation

HRID 1019449 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].O1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=O.O(C)[Na].[CH2:21]1COC[CH2:22]1>>[C:12]1([CH:16]=[CH:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:22]=[CH:21][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 7362FurfuralHCID 8028TetrahydrofuranHCID 68490alpha-HydroxyacetophenoneHCID 178418582HCID 178418582, compound

Product 1

HCID 7189CinnamoylbenzeneYield 71%

Procedure

2.27 g (16.7 mmol) of 2-hydroxyacetophenone, 1.52 g of furan-2-carbaldehyde (15.8 mmol), and 10 ml of 25% wt NaOCH3 were reacted in 50 ml of dry THF to give 2.4 g (71%) of chalcone after purification. 1H NMR (300 MHz, CDCl3): δ 12.90 (s, 1H), 7.94 (d, d, J=1.5, 8.1 Hz, 1H), 7.71 (d, J=15.0 Hz, 1H), 7.58 (d, J=15.0 Hz, 1H), 7.58 (d. J=1.5 Hz, 1H), 7.51 (d, d, d, J=1.5, 7.2, 8.4 Hz, 1H), 7.04 (d, d, J=0.9, 8.4 Hz, 1H), 6.96 (d, d, J=8.1, 8.1 Hz, 1H), 6.79 (d, J=3.3 Hz, 1H), 6.56 (d, d, J=1.5, 3.3 Hz, 1H).

Sources & evidence

ORD record
ord-5515abc9007f420985f6858c5c139db8
Source dataset
uspto-grants-2014_05
Patent number
US08715761B2

Reaction notes

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