Acetic Anhydride → 7-(Acetyloxy)-3-phenyl-4H-1-benzopyran-4-one

HRID 603269Notes

Reaction equation

HRID 603269 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53768917-Hydroxyisoflavone

Product 1

HCID 7464497-(Acetyloxy)-3-phenyl-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Acetoxyisoflavone was prepared from 7-hydroxyisoflavone (2.6 g, 10.9 mmol), acetic anhydride (16 ml) and pyridine (3.0 ml) as described for 4′,7-diacetoxydaidzein. Yield: (2.5 g, 82%) m.p. 133° C. 1H NMR (CDCl3): δ 2.36 (s, 3H, OCOCH3), 7.18 (dd, 1H, J 2.2 Hz 8.6 Hz, H6), 7.31 (d, 1H, J 2.2 Hz H8), 7.39-7.57 (m, 5H, ArH), 8.00 (s, 1H, H2), 8.33 (d, 1H, J 8.6 Hz, H5). Mass spectrum: m/z 280 (M, 28%); 237-(98); 238 (57).

Sources & evidence

ORD record
ord-783334d30a3e4b94b6a0cefd5fac8cb4
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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