Dimethylformamide → Bis(2,4,6-trichlorophenyl) phenylpropanedioate
Reaction equation
[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)[CH:16]=[O:17].[C:19]([Cl:24])(=O)[C:20](Cl)=O.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[C:27]=1O>ClCCl>[C:1]1([CH:7]([C:8]([O:17][C:16]2[C:19]([Cl:24])=[CH:20][C:26]([Cl:25])=[CH:27][C:28]=2[Cl:33])=[O:10])[C:11]([O:13][C:31]2[C:26]([Cl:25])=[CH:27][C:28]([Cl:33])=[CH:29][C:30]=2[Cl:32])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a slurry of phenylmalonic acid (5.00 g, 27.8 mmol) in dichloromethane (7 mL) at room temperature was added a drop of N,N-dimethylformamide, followed by the dropwise addition of oxalyl chloride (9.09 g, 71.6 mmol) at such a rate to keep gas evolution under control. The reaction mixture was stirred for an additional hour at room temperature, during which time the reaction mixture clarified. 2,4,6-Trichlorophenol (15 g, 76 mmol) was added, and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated under vacuum, and methanol (100 mL) was added to the residue, which resulted in precipitation of a large amount of solid. The solid was collected by filtration, rinsed with methanol (80 mL) and air dried to give the title product as a white solid (13 g).
Workup
- stirringthe reaction mixture was stirred at room temperature for 18 h
- concentrationThe reaction mixture was concentrated under vacuum, and methanol (100 mL)
- additionwas added to the residue, which
- customresulted in precipitation of a large amount of solid
- filtrationThe solid was collected by filtration
- washrinsed with methanol (80 mL) and air
- customdried
Sources & evidence
- ORD record
- ord-b8b12d97c2ae4c438e60585c28ca67ca
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697707B2
Reaction notes
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