Acetoacetic Acid → HCID 9884853, compound

HRID 1724616Notes

Reaction equation

HRID 1724616 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](=[CH:10][C:11]([OH:18])=[CH:12][C:13]=3[CH3:17])[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:3]=[CH:4][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][C:11]([O:18][C:29](=[O:30])[CH3:28])=[CH:12][C:13]=3[CH3:17])[O:8][CH:7]=2)=[CH:19][CH:20]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 96Acetoacetic AcidHCID 7918Acetic AnhydrideHCID 98382587-hydroxy-3-(4-hydroxyphenyl)-5-methylchromen-4-one

Product 1

HCID 9884853HCID 9884853, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
107.5 °C

Procedure

A mixture of 4′,7-dihydroxy-5-methylisoflavone (1.51 g, 5.6 mmol), acetic anhydride (9 ml) and pyridine (1.7 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 water and recrystallised from methanol to yield 4′,7-diacetoxy-5-methylisoflavone as colourless prisms (1.8 g, 91%). m.p. 195-97° C., 1H NMR (CDCl3): δ 2.32 (s, 3H, OCOCH3), 2.35 (s, 3H, OCOCH3), 2.87 (s, 3H, Me), 6.92 (bs, 1H, H8), 7.12 (bs, 1H, H5), 7.16 (d, 2H, J 8.7 Hz, ArH), 7.55 (d, 2H, J 8.7 Hz, ArH), 7.89 (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 water
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-dc5f06688e6b41758b8c74f07db78828
Source dataset
uspto-grants-2009_02
Patent number
US07488494B2

Reaction notes

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