Acetoacetic Acid → HCID 9819870, compound

HRID 603271Notes

Reaction equation

HRID 603271 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[C:10]([CH3:18])[C:11]([OH:17])=[CH:12][CH:13]=3)[O:8][CH:7]=2)=[CH:4][CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].[CH3:28][C:29](CC(O)=O)=[O:30]>N1C=CC=CC=1>[C:21]([O:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[C:10]([CH3:18])[C:11]([O:17][C:29](=[O:30])[CH3:28])=[CH:12][CH:13]=3)[O:8][CH:7]=2)=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 96Acetoacetic AcidHCID 7918Acetic AnhydrideHCID 15126657HCID 15126657, compound

Product 1

HCID 9819870HCID 9819870, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
107.5 °C

Procedure

A mixture of 4′,7-dihydroxy-8-methylisoflavone (2.9 g, 10.8 mmol), acetic anhydride (18 ml) and pyridine (3 ml) was heated on 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 water and recrystallised from ethyl acetate to yield 4′,7-diacetoxy-8-methylisoflavone as colourless prisms (3.2 g, 84%). 1H NMR (CDCl3): δ 2.31 (s, 3H, CH3), 2.32, 2.39 (each s, 3H, OCOCH3), 7.13 (d, 1H, J 9.0 Hz, H6), 7.17 (d, 2H, J 8.7 Hz, ArH), 7.59 (d, 2H, J 8.7 Hz, ArH), 8.07 (s, 1H, H2), 8.19 (d, 1H, J 8.7 Hz, H5).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. customcrystallised from the solution
  3. filtrationThe product was filtered
  4. washwashed thoroughly with water
  5. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2acfdd6a4caf49db8479e4ff84e772e8
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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