Acetone → (+)-Pinocembrin

HRID 1948748Notes

Reaction equation

HRID 1948748 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[CH2:5]1[CH2:9][O:8][CH2:7][CH2:6]1.CN([CH:13]=[O:14])C.[CH3:15][C:16]([CH3:18])=[O:17]>C(O)(=O)C.C(O)C.C(#N)C.CO>[CH:5]1[CH:6]=[CH:7][C:5]([C@H:9]2[O:8][C:7]3[CH:18]=[C:16]([OH:17])[CH:15]=[C:13]([OH:14])[C:3]=3[C:1](=[O:4])[CH2:2]2)=[CH:6][CH:9]=1

Participants

9

Reactant 4

HCID 180Acetone2×HCID 3776IsopropanolHCID 6228DimethylformamideHCID 8028Tetrahydrofuran

Product 1

HCID 68071(+)-Pinocembrin

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

Referring to the preparation method of Example 1, using the mixture of isopropanol and THF (isopropanol:THF=2:1), the mixture of acetonitrile and DMF (acetonitrile:DMF=4:1), the mixture of methanol and acetone (methanol:acetone=3:2), the mixture of ethanol and acetonitrile (ethanol:acetonitrile=1:1), and the mixture of ethanol, acetone and glacial acetic acid (ethanol:acetone:glacial acetic acid=2:1:0.1) as the solvents, white crystalline of pinocembrin was obtained. The results of the experiments were shown in Table 7. Powder X-ray diffraction, DSC and IR analysis were performed on the obtained crystalline, and the results showed that the crystalline form obtained was α crystalline form of pinocembrin.

Workup

  1. customReferring to the preparation method of Example 1

Sources & evidence

ORD record
ord-885c9a0073ef4cbaae4f4355af7dc2ef
Source dataset
uspto-grants-2013_03
Patent number
US08399511B2

Reaction notes

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