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Malonic Acid → Bis(2,4,6-trichlorophenyl) propanedioate

HRID 251571
Notes
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Reaction equation

HRID 251571 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].[C:11]([OH:17])(=[O:16])[CH2:12][C:13]([OH:15])=O.O=P(Cl)(Cl)Cl.O>CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[O:10][C:13](=[O:15])[CH2:12][C:11]([O:17][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[Cl:9])=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 962WaterHCID 69142,4,6-TrichlorophenolHCID 24813Phosphorus oxychloride

Product 1

HCID 2783450Bis(2,4,6-trichlorophenyl) propanedioate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2,4,6-trichloro-phenol (157.6 g, 0.8 mol), malonic acid (52 g, 0.5 mol), and POCl3 (98 mL, 1.05 mol) is heated at reflux for 4 hours. The reaction mixture is cooled slightly and poured into a mixture of ice, water, and ether with stirring. The solid is collected by filtration and dried in vacuo to give malonic acid bis(2,4,6-trichloro-phenyl)ester.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture is cooled slightly
  4. filtrationThe solid is collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c846da792c1f478ea146637bf7914fc8
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863454B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes