Dibenzoylmethane → Tribenzoylmethane

HRID 268507

Reaction equation

HRID 268507 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)C.[C:33]([CH:36]([C:42]([CH3:44])=O)C(OCC)=O)(=O)[CH3:34].[C:45]([C:48]1([C:54](OCC)=O)[CH2:52][CH2:51][CH2:50][C:49]1=O)(=[O:47])[CH3:46].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:45]([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:47])[CH3:46]

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-acetyl-acetoacetate, 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-9f27d11f015549b89859d82d99f296af
Source dataset
uspto-grants-1976_03
Patent number
US03947488

Linked notes

Loading…