Acetoacetic Acid → HCID 9799644, compound

HRID 1724613Notes

Reaction equation

HRID 1724613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH:7]=[C:6]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:5]2=[O:20].[C:21](OC(=O)C)(=[O:23])[CH3:22].[CH3:28][C:29](CC(O)=O)=[O:30]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:21](=[O:23])[CH3:22])[O:8][CH:7]=[C:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:29](=[O:30])[CH3:28])=[CH:15][CH:14]=1)[C:5]2=[O:20]

Participants

5

Reactant 3

HCID 96Acetoacetic AcidHCID 7918Acetic AnhydrideHCID 9882420HCID 9882420, compound

Product 1

HCID 9799644HCID 9799644, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
107.5 °C

Procedure

A mixture of 6-chloro-4′,7-dihydroxyisoflavone (1.25 g, 4.3 mmol), acetic anhydride (7.5 ml) and pyridine (1.4 ml) was heated in an oil bath at 105-110° C. for 1 h. After cooling the mixture to room temperature, it was stirred for a further 30 min during which time the diacetate crystallised from the solution. The product was filtered, washed thoroughly with aqueous methanol (50%) and dried to yield 6-chloro-4′,7-diacetoxyisoflavone (1.2 g, 75%) as colourless prisms. 1H NMR (CDCl3): δ 2.32 (s, 3H, OCOCH3), 2.41 (s, 3H, OCOCH3), 7.16 (d, 2H, J 8.6 Hz, ArH), 7.36 (s, 1H, H8), 7.57 (d, 2H, J 8.6 Hz, ArH), 8.00 (s, 1H, H5), 8.37 (s, 1H, H2).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. customcrystallised from the solution
  3. filtrationThe product was filtered
  4. washwashed thoroughly with aqueous methanol (50%)
  5. customdried

Sources & evidence

ORD record
ord-c92830879c4948659fe95d142bfda8ba
Source dataset
uspto-grants-2009_02
Patent number
US07488494B2

Reaction notes

Loading…