Dibenzoylmethane → Tribenzoylmethane

HRID 329312

Reaction equation

HRID 329312 reaction equation
[C:1]([O:7]CC)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[C:10]([CH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20])(OCC)=O.C[CH:22]([C:26](=O)[CH3:27])[C:23](=O)[CH3:24].[C:29](F)(=[O:31])[CH3:30].[C:33]([CH:36]([C:42]([CH3:44])=O)C(OCC)=O)(=O)[CH3:34].C([C:48]1([C:54](OCC)=O)[CH2:52][CH2:51][CH2:50][C:49]1=O)(=O)C.C(C(C)(C(=O)C)C(=O)C)(=O)C.C(CC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(F)(=O)C1C=CC=CC=1>>[C:16]([CH:2]([C:1](=[O:7])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:48][CH:54]=1)[C:3](=[O:4])[C:5]1[CH:27]=[CH:26][CH:22]=[CH:23][CH:24]=1)(=[O:20])[C:15]1[CH:10]=[CH:29][CH:17]=[CH:18][CH:19]=1.[C:29]([CH:2]([C:1](=[O:7])[C:10]1[CH:15]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:4])[C:5]1[CH:44]=[CH:42][CH:36]=[CH:33][CH:34]=1)(=[O:31])[CH3:30]

Participants

11

Reactant 9

HCID 8433Dibenzoylmethane2×HCID 8868Ethyl AcetoacetateHCID 11204Acetyl fluoride2×HCID 67999Benzoyl fluorideHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 699493-Methyl-2,4-pentanedioneHCID 79063Ethyl 2-acetylacetoacetateHCID 121311812,4-Pentanedione, 3-acetyl-3-methyl-HCID 214389482-Acetyl-2-carbethoxycyclopentanone

Product 2

HCID 413869TribenzoylmethaneHCID 7863132-Benzoyl-1-phenyl-1,3-butanedione

Procedure

When the thallous salts of ethyl acetoacetate, 2 -carbethoxycyclopentanone, and 3-methylpentane-2,4-dione, prepared according to Example 1, are treated with acetyl fluoride at room temperature as described in Example 4, ethyl 2-acetylacetoacetate, 2-acetyl-2-carbethoxycyclopentanone, and 3-acetyl-3-methylpentane-2,4-dione, respectively, are obtained in 95% yield. Tribenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with benzoyl fluoride in the same manner. Acetyldibenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with acetyl fluoride.

Workup

  1. customrespectively, are obtained in 95% yield

Sources & evidence

ORD record
ord-ace45aea84a44b808e0328f82d8e5541
Source dataset
uspto-grants-1977_04
Patent number
US04020073

Linked notes

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