Malonic Acid → HCID 11068325, compound

HRID 2081273Notes

Reaction equation

HRID 2081273 reaction equation
[C:1](O)(=O)CC(O)=O.[Cl:8][C:9]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:10]=1[O:11][C:12]1[CH:22]=[C:16]2[C:17]([O:19][C:20](=[O:21])[C:15]2=[CH:14][CH:13]=1)=[O:18].C(N(CC)CC)C.C(OCC)(=O)C>O>[Cl:8][C:9]1[CH:26]=[C:25]([C:27]([F:29])([F:28])[F:30])[CH:24]=[CH:23][C:10]=1[O:11][C:12]1[CH:22]=[C:16]2[C:15](=[CH:14][CH:13]=1)[C:20](=[O:21])[O:19][C:17]2([OH:18])[CH3:1]

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 3800858HCID 3800858, compound

Product 1

HCID 11068325HCID 11068325, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Dried malonic acid (156 g, 1.5 mol) and 5-(2-chloro-4-trifluoromethylphenoxy)phthalic anhydride (342 g, 1.0 mol) were stirred with triethylamine (200 ml) under a nitrogen atmosphere and warmed slowly to 80° C. After 5 hours at 80° C., the reaction mixture was allowed to cool to room temperature and ethyl acetate (750 ml) and water (500 ml) were added. The organic phase was separated and washed with dilute hydrochloric acid then water. Ethyl acetate was distilled from the solution and the crude product purified by chromatography over silica gel. Finally, crystallisation from 40°-60° petroleum spirit/diethyl ether afforded the product as a white solid, m.p. 106°-108° C. Yield=154 g (43%).

Workup

  1. temperatureto cool to room temperature
  2. customThe organic phase was separated
  3. washwashed with dilute hydrochloric acid
  4. distillationEthyl acetate was distilled from the solution
  5. customthe crude product purified by chromatography over silica gel
  6. customFinally, crystallisation from 40°-60° petroleum spirit/diethyl ether

Sources & evidence

ORD record
ord-33e7eca686834034a755c7f000e97463
Source dataset
uspto-grants-1993_02
Patent number
US05183907

Reaction notes

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